Review Article Function of Nanocatalyst in Chemistry of Organic Compounds Revolution ...downloads.hindawi.com/journals/jnm/2013/341015.pdf · 2019-07-31 · Review Article Function

Hindawi Publishing CorporationJournal of NanomaterialsVolume 2013 Article ID 341015 23 pageshttpdxdoiorg1011552013341015

Review ArticleFunction of Nanocatalyst in Chemistry of Organic CompoundsRevolution An Overview

Kanagarajan Hemalatha1 Gunabalan Madhumitha1 Amir Kajbafvala2

Narayanan Anupama1 Rajesh Sompalle3 and Selvaraj Mohana Roopan3

1 Organic Chemistry Division School of Advanced Sciences VIT University Vellore Tamil Nadu 632 014 India2Department of Materials Science and Engineering North Carolina State University Engineering Building I RaleighNC 27695-7907 USA

3 Chemistry Research Laboratory Organic Chemistry Division School of Advanced Sciences VIT University VelloreTamil Nadu 632 014 India

Correspondence should be addressed to Selvaraj Mohana Roopan mohanaroopansvitacin

Received 2 April 2013 Accepted 21 April 2013

Academic Editor Minghang Li

Copyright copy 2013 Kanagarajan Hemalatha et alThis is an open access article distributed under the Creative Commons AttributionLicense which permits unrestricted use distribution and reproduction in anymedium provided the originalwork is properly cited

Heterocyclicmotif is an important scaffoldwhich has both industrial andpharmaceutical applicationsThesemotifs can be preparedusing wide variety of reaction conditions such as the use of expensive catalyst toxic solvent harsh reaction condition like the use ofbase high temperature andmultistep reaction Although variousmethods are involved the chemistry arena is now shifted towardsthe greener way of synthesis Nanocatalyst constitutes an important role in the green synthesis This is because the activity of thecatalyst resides in the exposed portion of the particles By decreasing the size of the catalyst advantages such as more surface areawould be exposed to the reactant only negligible amount would be required to give the significant result and selectivity could beachieved thereby eliminating the undesired products The current review enlists the various types of nanocatalyst involved in theheterocyclic ring formation and also some other important functionalization over the ring

1 Introduction

The new era of chemistry is shifting towards the path ofinnovative techniques which mainly concentrates on envi-ronmental aspects [1 2] Each and every component of thereaction is investigated on the basis of ecofriendly conceptssuch as use of nonhazardous solvent (water) and solvent-free synthesis or inexpensive catalyst without affecting theyield and quality of the reaction Synthesis of heterocycliccore constitutes the important portion of organic synthesisbecause it has wide variety of pharmacological actions [3ndash6]Various methods have been adopted for the synthesis whichincludes the use of catalyst [7 8] ultrasound irradiation[9ndash11] and microwave irradiation [12 13] Although thesemethods have their own advantages it also possesses cer-tain disadvantages like expensive instruments inaccessiblematerials nonrecyclable and non-selectivity and so forth Toovercome these the role of nanocatalyst holds its application[14]Nanoscience is the cramof phenomenonon ananometer

range Atoms are a few tenths of a nanometer in diameterand molecules are typically a few nanometers in size Thesmallest structures humans have beenmade have dimensionsof a few nanometers and the smallest structures we willever make will have the dimensions of a few nanometersThis is because as soon as a few atoms are placed next toeach other the resulting structure is a few nanometers insize Chemistry is the study of molecules and their reactionswith each other Since molecules typically have dimensionsof a few nanometers almost all of nanoscience can bereduced to chemistry Chemistry research in nanotechnologyconcerns carbon nanotubes self-assembly C

60molecules

and structures built using DNA Sometimes the chemicaldescription of a nanostructure is insufficient to describe itsfunction Owing to the hasty progress of nanoscience andnanotechnology the primeval colloid science is given a newlife Because of their great differences from single moleculesand bulk materials nanoscale materials including colloidshave attractedmuch attention since the last decade especially

2 Journal of Nanomaterials

Application of

nanoparticles

Quinoxaline

Pyrazole Acridine

Isoquinolinones

123-Triazoles

Coumarins

Naphthoxazinones

Pyran Pyridine

Diazepines

Xanthene

Quinoline

Miscellaneousreaction

Benzo[b]furance

Figure 1 Application of nanoparticles in organic synthesis

NH2R

minusH2O

Figure 2 Possible mechanism for the formation of N-arylhomophthalimide 242

O O

S

NNH

NO

Anti-inflammatory

(a)

O O

S

NN

Antiallergic

O

Cl

(b)

O O

S

NN CH

Anticoagulant

(c)

O O

Antitumor

ONH

NR

O

(d)

Figure 3 Pharmacological activities of coumarins

Journal of Nanomaterials 3

N

Cl

Cl

ZnO nanorod

NH

O

N

O

KCl

N Cl

N

O+ KOH

K+

+ H2O

+

Figure 4 Role of ZnO nanorods in synthesis of N-alkylated products (adapted from [1])

N

N

O

N

N

O

N

N

O

N

Cl

Cl

N

N

O

N Cl

KOH

Fe nanoparticle

minus

minus

KCl + H2O

Figure 5 Role of Fe nanoparticles in N-alkylation reaction (adapted from [2])

in the field of catalysis Over the several past decades catalystsand catalytic reactions have attracted considerable attentionwith the aim of finding meaningful applications in the phar-maceutical and fine chemical industries The nanocatalystsare highly selective reactive and stable thereby it supersedesthe conventional catalyst Nanoparticles with a diameter ofless than 10 nm have generated intense interest over the pastdecade due to their high potential applications in areas such

as sensors nanoscale electronics catalysis and optics Thecatalytic activity of nanoparticles is affected by size thereforethe relative ratio of surface atom types changes dramaticallywith varying particle size Inmany cases the activity increasesas the particle size decreases due to favorable changes inthe electronic properties of surface atoms which are locatedmainly on edges and corners in small particles On the otherhand the reactivity and selectivity of metal nanocatalysts


also depend strongly on the different crystallographic planespresent on the nanoparticles and which can be achieved bycontrolling the morphology of these nanoparticles Size andsurface of the nanocatalyst play a major role because it is thereason for its selectivity and reactivity Also in some cases theenhancement by doping and surface chemical modificationswould be done to increase its performance [15] Nanocatalystis not only used in organic transformation but also it has vari-ous applications [16 17]These nanocatalysts can be preparedby various methods such as thermal decomposition micro-arc oxidation irradiation chemical vapor synthesis non-sono and sonoelectrooxidation sol-gel technique chemicalprecipitation photochemicalmethod hydrothermalmethodantisolvent precipitation glow discharge plasma electrolysiswet-chemical method microwave irradiation and sono-chemical method [16ndash21]The size and nature of nanocatalystvaries on the type of method used for preparation [22ndash27]Based on the requirement the method of preparation canbe selected In this paper we will review recent examplesof nanoparticles used in organic transformation such asquinoxaline naphthoxazinones coumarins 123-triazolesacridine pyrazole and isoquinolinones (Figure 1) The heartand soul of this paper is Section 223 where we covermiscellaneous functionalization on heterocycles this is achallenge for nanocatalyst researchers to engage

2 Application of Nanoparticles inOrganic Synthesis

21 Synthesis of Quinoxaline Analogues Quinoxaline is animportant chemical entity which has interesting biologicalproperties such as trypanocidal property [28] antimycobac-terial agent [29] and cytotoxic agent [30] The synthesis ofquinoxalines (Scheme 1) was carried out by oxidative cou-pling of 12-diamines 211 and 12-dicarbonyl compounds212 using gold nanoparticles supported on nanoparticulatedceria (AuCeO) or hydrotalcite (AuHT) as catalysts andair as an oxidant The use of nanoparticles led to the mildreaction conditions such as base-free reactions using mildtemperature and air as an oxidant The catalyst could bereused only with a little loss in activity [31] The use ofinexpensive and recyclable SiO

2which has highly reactive

ndashOHgroupon its surface has its application in the synthesis ofquinoxaline and it produces high yield in less reaction timeBecause of its reusable nature it supersedes the other catalyst[32] Quinoxalines can also be synthesized by advantageousnano-BF

3sdotSiO2and nano-TiO

2catalyst systemsThe reaction

was carried out at varied temperatures and different moles ofreactants to optimize the reaction condition and concludedthat solvent-free conditions at room temperature could bethe optimal one In addition the report concluded that thereaction time could be reduced by performing the reactionunder sonication [33] In nano-TiO

2system the same authors

carried out the synthesis in the presence of nano-TiO2and

compared with bulk TiO2and other applied catalysts The

satisfactory results were obtained in solvent-free condition atroom temperature using 12mol as a catalyst [34] Lu andcoworkers synthesized quinoxalines using magnetic Fe

3O4

nanoparticles The result shows that the reaction could be

performed well in water using 10 Fe3O4nanoparticles as

catalyst at room temperature and the catalyst can be recov-ered easily by using external magnet and reused with consis-tent activity [35] PolyanilineSiO

2nanocomposite material

was prepared and it was used as a catalyst for the synthesisof quinoxalinesThey reported that 10 catalyst was found tobe optimal for the reactant transformation and the catalystactivity was found to be consistent even after three runs [36]Another popular method to synthesize quinoxalines is byusing TiO

2nanoparticles as a catalyst The optimal protocol

system was found out by using dichloroethane as an efficientsolvent with 25mol catalyst to give the highest yield Alsoo-phenylenediamine with electron-withdrawing group gavethe higher rates and yield than the electron-donating groups[37] The quantitative yield of quinoxaline was obtained in 10minutes by using acetonitrile solvent system 10mol of Ni-nanoparticles as catalyst at 25∘C stirred under N

2atmosphere

[38] Bardajee and coworkers prepared SBA-15 supported onPd (II) Schiff-base complex nanocatalyst for the synthesis of2 3-disubstituted quinoxalines derivatives [39]

22 Synthesis of Pyrazole Analogues Pyrazole is an importantnovelty which has reported insecticidal [40] antimalar-ial [41] anti-inflammatory and antimicrobial [42] activi-ties Khan and coworkers synthesized 1-(45-dihydropyrazol-1-yl) isoquinolines 223 from chalcones 222 and 1-hydrazinylisoquinoline and 221 using iron-oxide nanopar-ticles and this method of synthesis eliminates the autoox-idation of the desired pyrazolines to the correspondingpyrazoles (Scheme 2) [43] (120572-Fe

2O3)-MCM-41 catalysts is

impregnated with 10 of iron oxide nanoparticles as arecoverable and reusable catalyst (Scheme 3) for the synthesisof pyrazolo [34-c] pyridine 226 derivatives from 35-dibenzylidenepiperidin-4-one 224 and hydrazine deriva-tives 225andashc The optimum amount of catalyst was foundto be 0015 g and further increase in the amount of catalysthas no effect on rate of the reaction and yield Even thoughpure MCM-41 amino-functionalized MCM-41 and Fe

3O4

produced satisfactory result the ease of recoverability andreusability of (120572-Fe

2O3)-MCM-41 made it to prefer this

catalyst for the pyrazole analogue synthesis [44]

23 Synthesis of Acridine Analogues Acridine one of theimportant nitrogen heterocycle shows activity such as anti-herpes [45] antimalarial and antitumor [46] and larvicidalaction [47] Roopan and Khan performed an ecofriendlysynthesis of 9-chloro-6 13-dihydro-7-phenyl-5H-indolo [32-c]-acridines 233 by Friedlander condensation (Scheme 4)of 2-amino-5-chlorobenzophenone 231 and 34-dihydro-2Hcarbazol-1(9H)-one and 232 in the presence and absenceof SnO

2nanoparticles under microwave irradiation The

reaction was not initiated in the absence of catalyst [48] Acomparative study of various nanoparticles (Mn

3O4 CuO

CaO MgO and Fe3O4) optimization of solvent and tem-

perature showed that nano-Fe3O4(10mol ) + solvent-

free conditions + 120∘C as an efficient protocol for thesynthesis (Scheme 5) of 18-dioxo-decahydroacridines 236from aldehyde 235 dimedone 234 and aromatic amine


O

O N

N

Ph

Ph

(i)

NH2

NH2

(i) Au SiO2 BF3-SiO2 Fe3O4 polyanilineSiO2 TiO2 Ni PdSBA-15

+

211 212 213

Scheme 1 Synthesis of quinoxaline analogues 213

NCl

N

N

Cl

N

O

222221 223

(ii)

H2NHN

+

(ii) Iron oxide ethanol 30min reflux

Scheme 2 Synthesis of pyrazole analogues 223

N

O

225a

225b

225c224

N

N

226

NR

(iii)

NHNH2

NHNH2 Ac2O

CH3NHNH2

(iii) (120572-Fe2O3)-MCM-41-SO3H ethanol 30min rt

Scheme 3 Synthesis of pyrazole analogues 226 using dibenzylidenepiperidin-4-one

Cl O

HN

O

N

HN

Cl

(iv)

231 232 233

NH2

+

(iv) SnO2 nanoparticles H2SO4 500W MW

Scheme 4 Synthesis of acridine analogues 233 using 2-amino-5-chlorobenzophenone


O

O

O

(v)

(vi)

NH

O O

236

N

O OPh

237

234 235

(v) NH4OAc MCM-41 SO3H solvent free 110∘C(vi) Aniline Fe3O4 solvent free 120∘C

+

C6H5

Scheme 5 Multicomponent strategy to synthesis acridine analogues 236-237

(vii)

(viii)241

COOH

COOH

N

O

O

N

O

X

242

243

(vii) Aniline ZnO nanoparticles toluene reflux

(viii) C6H4NH2NH2 (or) NH2C6H4OH (or) NH2C6H4SH ZnO nanoparticles toluene reflux

X = O S NH

Scheme 6 Synthesis of N-arylhomophthalimides 244 and Isoquinolinones 245

in the presence of ammonium acetate [49] 0005 g of MCM-41-SO

3H 110∘C and solvent-free condition is another effec-

tive combination for obtaining 1 8-dioxo-9-aryl decahy-droacridines nucleus 237 [50]

24 Synthesis of N-Arylhomophthalimides and BenzannelatedIsoquinolinones Isoquinolinones are reported to causeallosteric modulation of metabotropic glutamate receptor 2[51] and also it has JNK inhibitory action [52] An emeraldprocedure was developed utilizing an efficient catalystthat is ZnO nanoparticles mediated the synthesis of N-arylhomophthalimides and benzannelated isoquinolinonesKrishnakumar and coworkers synthesized flower-shapedZnO nanoparticles and used them in the reaction betweenhomophthalic acid 241 and substituted anilines benzylamine for the ecofriendly synthesis of N-arylhomoph-thalimide 242 and benzannelated isoquinolinones 243(Scheme 6) They carried out the reaction using variouscatalysts solvents and different concentration of the catalystNano ZnO at a concentration of 5mol in the toluene systemwas found to be effective [53]The ZnO nanoparticles exhibit

admirable catalytic action and the proposed methodologywas capable of providing the desired products in good yieldand purity The possible mechanism for the formation of thisproduct is illustrated in Figure 2

25 Synthesis of 14-Disubstituted 123-Triazoles 123-triazoles (Scheme 7) an important entity has reported anti-mycobacterial activity [54] anti-HSV-1 activity [55] andantifungal activity [56] This moiety can be synthesizedby an innovative concept called ldquoclick chemistryrdquo It is areaction between sodium azide 251 and alkyne to give14-disubstituted 123-triazoles in the presence of copper andwater This reaction is also known as Cu-catalyzed alkyneazide cycloaddition Since copper acts as a catalyst in thesynthesis of triazoles copper supported on various materialscan be made into nanoparticles and its yield and specificitycan be increased further Alonso and coworkers synthesized123-triazoles through various heterocycles derived fromnatural product such as (ndash)-menthol lactic acid D-glucoseoestrone and cholesterol converting them into alkynesby introducing propargyl groups Propargyl methyl ether


251

O

252

Br

253O

Br

254

255

O

256

BHO

HO

257

NN

N

R258

Na+NminusminusN

R1

N+

Phenacyl bromide254

phenylacetylene255 and sodium

azide 251

Styrene oxide256

sodium azide251 and

phenylacetylene255

Propargyl methylether 252

benzyl bromide253 and sodium

azide 251

Arylboronic acids257 sodium

azide 251 andphenylacetylene

255

123-

triazole

Benzylbromide253 sodium


255

Scheme 7 Synthesis of 123-triazoles 258 using various strategy

OH

O

+ O

OEtO O

261 262 263

(ix)

R1

R1

R2

R3

R3 R4

R2

R4

(ix) ZnO nanoparticles MWR1 = H OH OMeR2 =

R3 = H Cl Br NO2 OHR4 = CO2Et COMe CN

H OH OMe Et2N

Scheme 8 Synthesis of coumarins 263

252 benzyl bromide 253 and sodium azide 251under click reaction condition to give triazole derivativesThese derivatives of natural products having wide varietyof application were obtained in high yield using coppernanoparticles [57] CuI supported on poly(4-vinylpyridine)[P4VPy-CuI] acts as a heterogenous catalyst for the synthesis

of triazoles Using the optimized ratio of 1 1 11 of phenacyl

bromide 254 phenyl acetylene 255 and sodium azide251 01 g of P

4VPy-CuI and water required triazoles

were obtained after refluxing Also this catalyst can bereused up to 8 runs without losing its efficiency [58]Metalloanthraquinone complex an important catalyst forthe synthesis of 14-disubstituted 123-triazole was preparedand various reaction conditions were studied Various metal


O O OO O

OH R OH

O

OH

(x)

271 272 273

RCHO+

R = 4-ClC6H4 4-NO2C6H4 4 and 2-OHC6H4 34(CH3O)2C6H3(x) PVP-Ni ethylene glycol rt

piperonyl

Scheme 9 Synthesis of biscoumarins 273

OO HO

(xi)O

HNO

281 282 283284

H2N NH2

++

(xi) Cu nanoparticles K2CO3 PEG-400

Scheme 10 Synthesis of naphthoxazinones 284

NC CN (xii)

291 292

O

O

RNC CN

293

O

R

O

NC CNCN

NH2

+

R = Alicyclicheterocyclic(xii) TiO2 NPs H2O RT

Scheme 11 Synthesis of pyran analogues 293

NC CN

294 295

(xiii)(xiv)(xv)

(xvi)

O

OArNC

EtOOC

298

O

CNAr

EtOOC

2911

299

O

O

O

Ar

CN

2910

H3C

NH2

NH2

(xv) Dimethylcyclohexane-13-dione 296 Fe2O3

(xvi) ZnO nanoparticles(xiii) 4-Hydroxy-2H-chromen-2-one 297 CuO(xiv) 4-Hydroxy-2H-chromen-2-one 297 Fe2O3

+

COCH3

H2N

PhndashCHO

Scheme 12 Multicomponent reaction for the construction of pyran analogues 299ndash2911


N

O

2912

N

O

2913

NC CN

295

(xvii)

CN

(xvii) MCM-41-SO3H solvent free

+

NH2

Scheme 13 Synthesis of pyrano pyridine 2913

NN

CHOMeO OMe

O O

N N

NH

Cl

Me Me

Cl

(xviii)

2101

2102

2103 2104

AcONH4

+

+

MeO2C CO2Me

(xviii) MgO nanotube CH3CN reflux

Scheme 14 Synthesis of 14-dihydropyridine derivatives 2104

O

NH

HN O

2111 2112 2113 2114(xix)

H2N NH2

R2

R2

R2

R3

R3

R3

+ +R1

R1

R4

R1 =

R2 and R3 = acetone cyclohexanone acetophenoneR4 = aliphatic alicyclic aromatic(xix) Fe3O4SiO2 EtOH rt 3ndash6 h reflux

R4ndashNC

CN ArndashCl2 ArNO2 ArndashCOOH

Scheme 15 Synthesis of diazepines 2114

CHO

OH

O

Ph

NH

O N

O

2121 2122 2123 2124

(xx)

(xx) CuI nanoparticles K2CO3 reflux 15h

+ +

Scheme 16 Synthesis of benzo[b]furans 2124


CHO

O

OO

2131 2133

(xxi)

O

O

2132

NO2

NO2

+

(xxi) MCM-41-SO3H H2O sonication

Scheme 17 Synthesis of 18-dioxo-octahydroxanthenes 2133

N

OCN

CN

N

N

NHCN

2141 2142 2143 2144

(xxii)Cl Cl

Cl Cl

+ +

NH2

(xxii) 120572-Fe2O

3-MCM-41-SO

3H solvent free120∘C

Scheme 18 Synthesis of 16-naphthyridine analogues 2144

ligands complexes were tested but only copper was foundto be catalytically active due to the richness of electron onmetal Water was found to be an effective solvent and alsothe amount of water is also an important criterion Theoptimum amount of water required was found to be 5mLfor the reaction between styrene oxide 256 sodium azide251 and phenyl acetylene 255 [59] Another environmentfriendly synthesis of triazoles was the cyclisation reactionbetween three components benzyl bromide 253 sodiumazide 251 and phenyl acetylene 255 in the presenceof magnetically separable CuFe

2O4nanoparticles water

at 70∘C The catalyst can be separated easily and reusedeffectively [60] In an alternative method various coppersalts [CuI CuSO

4 CuCl

2 Cu (NO

3)2 Cu2-120573-CD complex]

were used for the synthesis of 123-triazoles of phenylboronic acid from coupling of aryl boronic acids 257sodium azide 251 and phenyl acetylene 255 Amongthese cooper catalyst Cu

2-120573-CD complex gave excellent yield

of 123-triazole 258 without adding any additives [61]

26 Synthesis of Coumarins Coumarins are attractive mol-ecule in chemistry with anti-inflammatory activity [62]antioxidant and lipoxygenase inhibitory activity [63] andantifungal activity [64] Coumarin has been used as an aromaenhancer in pipe tobaccos and alcoholic drinks althoughin general it is banned as a flavorant food additive due toconcerns about coumarinrsquos hepatotoxicity in animal modelsThe synthesis of coumarins and its analogues has attracted

extensive thought from organic and medicinal chemists formany years as a large number of natural products con-tains this heterocyclic nucleus Moreover coumarins havevarious pharmacological activities (Figure 3) Knoevenagelcondensation is one of the widely used reactions for thesynthesis of coumarins (Scheme 8) Since it involves theuse of acids and bases an alternative approach for carryingout the condensation is essential The reaction between o-hydroxy benzaldehyde 261 and 13-dicarbonyl compounds262 is an effective reaction for the formation of coumarins263 ZnO nanoparticles were found to be an effectivealternative in 10mol concentration Increase or decrease inthe concentration of the ZnO extends the time taken for thereaction with fewer yields [65]

27 Synthesis of Biscoumarins Transition metal nanopar-ticles have gained tremendous importance due to theirinteresting electrical optical magnetic chemical propertiesand especially catalytic properties which cannot be achievedby their bulk counterparts Recently there has been growinginterest in using nickel nanoparticles in organic synthesisowing to their easy preparation potent catalytic activity pos-sible process ability and high stability Heterocyclic systemsare common structural motifs in many biologically activesubstances and natural products and therefore warrant thedesign of newer and efficient protocols for their synthesis Inview of this biscoumarins is an important molecule whichpossesses anticoagulant activity (Scheme 9) [66] Khurana


XH(xxiii)

CHON

XR

NH2

+ R1

X = N 2151X = S 2152

R1 = 2153

(xxiii) CdSMn-doped CdS nanoparticles Au nanoparticlesC stirring90

∘C

X = NH 2154

R1 = Cl NO2 Me OMe

X = S 2155

Scheme 19 Synthesis of benzimidazoles 2154 and benzothiazoles 2155

O

O

Ph

Ph

2161

CHO

2162 2163

(xxiv)

NN

PhPh

2164

+ + NH2

(xxiv) TiCl4 SiO2 SBA-Pr-SO3H MgAl2O4 sulfated zirconia MCM-41-SO3H Fe2O3

Scheme 20 Synthesis of imidazoles 2165 and 2166

and Vij performed the synthesis of biscoumarins 273via Knoevenagel condensation followed by rapid Michaeladdition using polyvinyl pyrrolidone-(PVP)-stabilized nickelnanoparticles for the reactions of aldehydes 271 with 4-hydroxycoumarin 272 in ethylene glycol at room tempera-ture [67]

28 Synthesis of Naphthoxazinones Naphthoxazine an im-portant motif in heterocyclic chemistry has reported cyto-toxic and antifungal activities [68] An efficient protocol forthe synthesis of 2-naphthol-condensed 13-oxazinone 284(Scheme 10) by the reaction between benzaldehyde 281urea 282 and 120573-naphthol 283 was carried out in thepresence of K

2CO3and copper nanoparticles stabilized by

PEG-400 In the absence of Cu the reactionwas not initiatedWhen the same reaction was carried out without PEG-400 the yield was only 30 Due to various drawbacks ofresults with the solvents such as DMSO acetonitrile ethanolTHF and ethylene glycol the ideal solvent for the synthesisof naphthoxazinones was found to be PEG-400 Not doesonly it act as a solvent but also it provides stability to Cunanoparticles [69]

29 Synthesis of Pyran Analogues Pyran has reportedactivities such as molluscicidal activity [70] and anthelminticactivity [71] The synthesis of pyran-annulated heterocyclicsystems 293 (Scheme 11) can be carried out from variousalicyclicheterocyclic 13-dione 291 and tetracyanoethyl-ene 292 using ecofriendly TiO

2and TiO

2nanoparticles as

a catalyst with high yield Because of the heterogenous natureof TiO

2 the work-up process will be carried out easily

and the catalyst can be recovered without any difficulty

[72] The three-component reaction between aromaticaldehyde 294 malononitrile 295 4-hydroxycoumarin297 and CuO nanoparticles (15mol) in 10mLwater is an effective protocol for the synthesis of 34-dihydropyrano[c]chromenes 2910 (Scheme 12) The samereaction was carried out in the presence of MgO ZnOand NiO but the reaction in the presence of CuO wasproved to be best in yield [73] Khoobi and coworkerscarried out the synthesis of 4H-benzopyrans 2911 and2-amino-5-oxo-4-aryl-45-dihydropyrano[3 2119888]chromene-3-carbonitriles 2910 (Scheme 12) using the new conceptof magnetically inorganic-organic hybrid nanocatalysthydroxyapatite-encapsulated Fe

2O3[74] A new way of

synthesizing 4H-pyrans 299 was carried out in ionic liquidusing ZnOMgO solid sample containing ZnO nanoparticlesas an innovative catalyst [75] The 120572-Fe

2O3nanopowder

was prepared by combustion method and it was used inthe synthesis of 34-dihydropyrano[c]chromenes 2910[76] MCM-41-SO

3H has functional groups which forms

bonding with 35-dibenzyl idenepiperidin-4-one 2912 andthe reactions are initiated inside the nanoreactor along withmalononitrile 295 The rate of the reaction is increased inthe compound 2912 with electron-withdrawing group anddecreases with electron-donating group The combinationof nanosized MCM-41-SO

3H and solvent-free atmosphere

for the ecofriendly synthesis of pyrano [3 2-119888] pyridinederivatives 2913 (Scheme 13) [77]

210 Synthesis of 14-Dihydropyridine Derivatives 14-dihy-dropyridine possesses activity such as calcium channel antag-onist activity [78] and antioxidant activity [79] Synthesisof pyrazolyl 14-dihydropyridines (Scheme 14) 2104 was


NC CN

NH

N

N

R

CN

CHO

X2171 2172 2173

2174

(xxv)+ + NH2

NH2

R998400

R998400

R998400

= Ph NH2

X = H Me Cl Br Me2N(xxv) CuO microspheres ZnO H2O rt

Scheme 21 Synthesis of pyrimidone carbonitriles 2174

O

R

N

NOAr

Ar

R

O

2181 2 182 2183 2184

(xxvi)+ + Ar-NH2

R = H CH3

(xxvi) (H14NaP5W30O110)SiO2 DMSO reflux

Scheme 22 Synthesis of spirohexapyrimidines 2184

carried out by multicomponent reaction between pyrazolyl-4-carbaldehyde 2101 acetoacetic ester 2102 ammoniumacetate 2103 using 15 MgO nanotube in the presence ofacetonitrile Even though the reaction was carried in varioussolvents usage of acetonitrile-made MgO nanotube gave theexpected product in high yield [80]

211 Synthesis of Diazepines The development of newapproaches for the construction of number of heterocyclecontinues to be essential for accessing natural products andtheir structural analogues Among them 1H-14-diazepinesderivatives scaffolds over the years have gained an ongoinginterest for biological activities as antileukemic antiviralantiplatelet anticancer anticonvulsant psychotropics andherbicidal [81 82] Maleki synthesized one-pot multicompo-nent synthesis of diazepine derivatives 2114 (Scheme 15)from readily available 12-diamine 2111 a linear or cyclicketone 2112 and an isocyanide 2113 using magneticallyrecoverable Fe

3O4SiO2nanocatalyst [83]

212 Synthesis of Benzo[b]Furans Furan ring possesses someimportant activity such as cytotoxic activity [84] and antibac-terial activity [85] An ecofriendly multicomponent synthesisof benzo[b]furans (Scheme 16) was carried by the conden-sation reaction between salicylaldehyde 2121 morpholine2122 and phenyl acetylene 2123 using copper iodidenanoparticles as a specific catalyst The reaction was stan-dardized with various aldehydes amines and acetylenesThe result concluded that salicylaldehyde with electron-

withdrawing groups aromatic alkynes and aliphatic aminesgave the desired benzo[b]furans [86]

213 Synthesis of 18-Dioxo-Octahydroxanthenes Octahy-droxanthenes act as anticancer agents [87] A classi-cal method for synthesis of 18-dioxo-octahydroxanthenes2133 (Scheme 17) was the condensation reaction between4-nitrobenzaldehyde 2131 and dimedone 2132 usinga combination of ultrasound irradiation and nanosizedMCM41-SO

3H catalyst which leads to increase in the rate of

the reaction and yield [88]

214 Synthesis of 16-Naphthyridine Analogues Naphthyri-dine derivatives are reported with antitumour activity [89]and antimicrobial activity [90] The reactants such as 35-bis(4 chlorobenzylidene)-1-methylpiperidin-4-one 2141 ani-line 2142 and malononitrile 2143 are mixed together insolvent-free condition A novel magnetic (120572-Fe

2O3)-MCM-

41-SO3H acts as a nanocatalyst which could be reused even

after 5 runs without decrease in activity This acts as anefficient catalyst for the synthesis of N-aryl-2 amino-16-naphthyridine derivatives 2144 (Scheme 18) [91]

215 Synthesis of Benzimidazoles and Benzothiazoles Themixture of o-phenylenediamine 2151 aminothiophenol2152 and aromatic aldehydes 2153 in water was stirredat 90∘C using prepared CdS and manganese-doped CdSnanoparticles for the chemoselective synthesis of benzim-idazoles 2154 (Scheme 19) and benzothiazoles 2155


OH

N

O OBase argon

2191 2192 2193

2195

OH

2194

(xxvii)

R1 R1

R1

+

+

R2R2

R2

R3

R3

R1 = R2 = Ph 234-MeC6H4 4-OMeC6 3C6H4

R3 = Me(xxvii) Ag-PdC base O2

NH2

H4 4-CF

Scheme 23 Synthesis of quinoline 2195

O

NH

COOH

NC CN N

OCN

NH

O

N

OCN

NH

O

O

NH

COOH

2196 2197

21982199

21910

21911

(xxviii)(xxviii)R1

R1R1

CHO +

R1 = C6H5 4-MeOC6H4 4-BrC6H4 4-ClC6H4 4-MeC6H4

(xxviii) CuO nanoparticles 50∘C 30ndash45min

Scheme 24 Synthesis of imidazo[12-119886]quinoline 21911 and quinolino[12-a]quinazoline 21910

The doping of Mn increased the activity and selectivity ofnanoparticles [92]

216 Synthesis of Imidazoles Imidazoles are present in vari-ous pharmacologically active compounds which act as anti-tuberculosis agent [93] and antibacterial agent [94] Theywere synthesized as either-trisubstituted or -tetrasubstitutedimidazoles by using various reaction conditions such asultrasonic irradiation [95] TBAB catalyst [96] and HClO

4-

SiO2catalyst [97] Imidazoles (Scheme 20) can also be

obtained by multicomponent reaction using benzil 2161aldehydes 2162 andamines 2163 in the presence of

metal nanoparticles as a catalyst TiCl4supported on silica

was used as a mild solid Lewis acid for the synthesis oftriphenylimidazoles This catalyst system can be preparedhandled and stored without any special precautions bymaintaining its efficiency They carried out the reactionunder solvent-free condition at 110∘C for 30 minutes [98]The solvent-free synthesis of imidazoles was explored withsulfonic acid functionalized SBA-15 as a catalyst It was foundthat aliphatic aldehyde gave moderate yield and the aromaticaldehyde with electron-withdrawing and electron-donatinggroups gave excellent yield in the presence of catalyst and itcould be recovered by continuous washing with dilute acidwater and acetone [99] Amild Lewis acid catalystMgAl

2O4


CHO

+NC

OO

2196 21912

(xxix)

N

CN

OH

21914

N

CN

OH

21915

21913R1

R1

NH2

NH2

(xxix) TiO2NPs MW

Scheme 25 Synthesis of quinoline-3-carbonitriles 21914 (or) benzo[h]quinoline-3-carbonitrile 21915

O

R X

N

R

X

O O

N

RO

O

21917

21916

21918

2191921920

(xxx) (xxx)NH2

R1

R2

R1

R2

R1 = R2 = H CH3

R = Ph CH3(xxx) CuO SiO2NPs stirring 60∘CX = CO2Et CO2Me CO2Bu COCH3

Scheme 26 Friedlander methodology to synthesis of quinoline analogues 21919-21920

was utilized for the efficient synthesis of substituted imida-zoles under ultrasound irradiation Because of the decreasein size of the crystal magnesium aluminate a defect wasproduced in the coordination of constituent atoms whichincreases the reactivity of the catalyst and thereby it leads tocyclocondensation reaction for the formation of imidazoles[100] The synthesis of imidazole was carried out using clayand zeolite and also with nanocrystalline-sulfated zirconiacatalyst in the presence of ethanol at room temperature Theoptimization of the reaction condition was performed andfound that the yieldwas increased up to 93by the SZ catalyst[101] The Bronsted acid nanoreactor MCM-41-SO

3H was

involved in the solvent-free synthesis of trisubstituted andtetrasubstituted imidazoles In this experiment it was foundout that the solvents have no role on the synthesis ofimidazolesThemodified action of the nanoreactor increasedits efficiency and resulted in higher yield and good reusability[102] An efficient catalyst magnetic Fe

3O4nanoparticles

can also be used for the synthesis of imidazole derivativesMagnetic Fe

3O4nanocatalyst and temperature (80∘C) play

a crucial role in this reaction under solvent-free conditionand gave a maximum yield of up to 96 [103] Rostamizadehand coworkers developed a toxic-free solvent reaction for thesynthesis of 245-trisubstituted and 1245-tetra-substitutedimidazoles using nanosizedMCM-41-SO

3Has a catalyst [88]

217 Synthesis of Pyrimidine Carbonitriles The three-com-ponent reaction involving aldehydes 2171 malononi-trile 2172 and amidines 2173 in the synthesis of 4-amino-5-pyrimidinecarbonitriles 2174 (Scheme 21) wascatalyzed using CuO microspheres CuO microspheres aremade by granulation of nanoparticles using immobilization-calcination method [104] Even though the surface area ofmicrospheres is lesser than nanoparticles they are largerthan bulkier substances The main purpose of microspheresis to avoid the physical instability of nanoparticles such asagglomeration The polar solvents such as THF CH

3CN

and CH3CH2OH gave fewer yields than water in the

synthesis of 4-Amino-5-pyrimidinecarbonitriles 4-amino-5-pyrimidinecarbonitriles can also be synthesized using ZnO


H N

O

(xxxi)

21913 2196 21921

+

NH2

R2

R2

R2

R1R1

R1 = CH3 CH(CH3)2 OCH3 Ph ClR2 = C6H5

(xxxi) AuNPSiO2 O2 bubbling 110∘C 6h

Scheme 27 Role of Gold and SiO2in quinoline synthesis 21921

O

O

+OHC

O

OO

NH

O

O

O(xxxii)

21918 21922 2162 21923

21924

(xxxii) Fe3O4-Cys EtOH 25min

OCH2Ph

OCH2Ph

OCH2Ph

OCH2Ph+ +NH4OAC

Scheme 28 Multicomponent approach in quinoline synthesis 21924

nanoparticles Being insoluble in water and other organicsolvents it can be easily recovered from the reaction mixtureimmediately after the reaction [105]

218 Synthesis of Spirohexahydropyrimidines Aone-pot con-densation of cyclohexanone 2181 ketone 2182 andaniline 2183 using innovative preyssler nanoparticlesH14[NaP5W30O110

]Si as an efficient catalyst system forsynthesizing 13-diaryl-5-spirohexahydropyrimidines 2184(Scheme 22) [106]

219 Synthesis of Quinoline Analogues Quinoline nucleusis one of the important constituents which is present inthe naturally occurring alkaloids It has proven antimalarialactivity along with many other important pharmacologicalactions In the synthesis of polysubstituted quinolines 2195(Scheme 23) first step involves the 120572-alkylation of ketone2192 with alcohol 2191 to give saturated ketone 2193In the second step ketone 2193 undergoes modifiedFriedlander annulations process with 2-aminobenzyl alcohol2194 to get the desired product Ag-Pd alloy nanoparticlessupported on carbon a comparison of the activity of Ag-PdC catalyst with that of palladium-based nanocatalysts-core-shell AgPdC and PdC were studied At 125∘C all thecatalyst produced more- or less-same yield whereas at 90∘CAg-PdC catalyst superseded the other two catalysts in yieldThis was explained due to the transfer of charge from less-electronegative Ag metal to more electronegative Pd [107]An alternative method to synthesize quinoline derivativessuch as imidazo[12-119886]quinoline 21911 and quinolino[12-a]quinazoline 21910 (Scheme 24) is to heat the mixture of

aldehyde 2196 malononitrile 2197 enaminones (21982199) at 50∘C for 30ndash45 minutes in the presence of knownsolid base catalysts bulk CuO and CuO nanoparticles Allthe catalyst is except CuO nanoparticles underwent reactionfor a long time with moderate to poor yield Whereas CuOnanoparticles produced excellent yield because of its insol-uble nature in water it can be recovered easily [108] TiO

2-

catalyzed synthesis of quinoline-3-carbonitriles 21914 (or)benzo[h]quinoline-3-carbonitrile 21915 and (Scheme 25)in the presence of water and microwave irradiation wascarried out in an ecofriendly way These derivatives can besynthesized from arylaldehyde 2196 cyanoacetate 21912anilines 21913 using knoevenagel condensation Michaeladdition followed by aromatization The report indicatedthat the nanocatalyst showed superior reactivity than theconventional method [109]

The optimization of Friedlander synthesis of quinolines(Scheme 26) was carried out on various of 2-aminoarylketones 21916 active methylene compounds 21917 andsimple cyclic ketones 21918 under different catalysts (TiO

2

SiO2 Al2O3 ZnO MgO CuO bulk and nano-CuO) in

solvent-free condition at 60∘C and nano-CuO was foundsuperior to all the other catalysts [110] So et al exploredthat AuNPsSiO

2+ O2as an efficient catalyst system for

the synthesis of polyheterocyclic compounds containingnitrogen 21921 (Scheme 27) from aniline 21913 andaldehyde 2196 They performed the mechanistic studies ofquinolines and reported that the reaction does not follow theradical pathway and the yield was very less in the presenceof silica alone Therefore AuNPsSiO

2+ O2protocol is the

optimal one for the quinoline synthesis [111] Ferritemagnetic


O

O

OH

O

O

NH

O

COOH21925 21926

21927

R1

R1

R2

R2

R2

R2

NH4OAc

R1 = Cl OCH3

R2 = H Me

+ +

CH3

TiO2 NPs

Scheme 29 Metal oxide-mediated quinoline analogue synthesis 21927

Y

XH

Y

X

HN O

2201 2202 2203

(xxxiii)

(xxxiii) CuO H2O stirring rt

NH2

+ RO2C CO2R

CO2R

X = S O NHR = CH3

Y = CH N C2H5

Scheme 30 CuO-mediated various benzoheterocycle synthesis 2203

O OMeMeON

R

R

O O

X

+N

N

X(xxxiv)

2211 22122213

2214 2215 2216

(xxxiv)

(xxxiv) Fe3O4 H2O MW 140∘C

NH2

+

R = Alkyl aryl heterocyclic

NHNH2

X = H Et ClR1

R1

= MemiddotOEt

Scheme 31 Synthesis of pyrrole 2213 and pyrazole 2216

INHR

R

2221 22222223

(xxxv)

(xxxv) 3 PdMIL-101

NH2

+

Scheme 32 Green synthesis of indole 2223


2231 2232

2233

N

O

N

OH

(xxxvi)

(xxxvi) Fe3O4 as catalyst

R1

R1

R2

R2

R3

R4

R4

R3

R5

R5

R1 = R2 = H MeR3 = H OMe Br CN NO2

R4 = H Et

R5 = H Cl Br FR6 = R7 = H

R6

R6

R7

R7

+

Scheme 33 C-alkylation of indole using Fe2O3 2233

R OR

OHR

Cl

N

N

O

N O

a

b

c

R

R

N

OEt

R

O

O

Cl

(xxxvii)2234 2235 2236

2237

2238

2239N Cl N Cl

NaBH4 SOCl2

a = 4(3H)-pyrimidoneb = piperidin-4-onec = ethyl 6-chloro 12-dihydro-2 oxo 4 phenylquinoline 3 carboxylate

R =

(xxxvii) ZnO nanorods reflux 110∘C

Scheme 34 Cross-coupling reaction 2237ndash2239

nanoparticles with cysteine can be used as catalyst for theHantzsch synthesis of hydroquinolines 21924 (Scheme 28)in a multicomponent reaction between 34 diphenoxy ben-zaldehyde 21922 ammonium acetate 2162 ethyl ace-toacetate 21923 and 55-dimethylcyclohexane-13-dione21918 The yield was up to 88 and it could be reusedwith unaltered activity until 9 cycles [112] Abdolmohammadideveloped and green friendly protocol for the synthesisof 5-oxo-4-aryl-145678-hexahydro-2-quinolinecarboxylicacid 21927 (Scheme 29) using TiO

2nanoparticles under

solvent-free conditions [113]

220 Synthesis of Benzoheterocycle Derivatives CuO nano-particles are capable of synthesizing various compoundswhich has both pharmacological and industrial applica-tions In the benzoheterocycles 2203 (Scheme 30) for-mation reaction between aromatic amine 2201 anddialkyl acetylenedicarboxylate 2202 catalyzed by CuOnanoparticles was optimized by various solvents (waterdichloromethane ethanol and acetonitrile) Water excels in

yield more than the other solvents CuO has both oil- andwater-resistant character So it can be reused by easy recyclingprocess without losing its efficiency [114]

221 Synthesis of Pyrrole and Pyrazole Nanoparticles com-bined with organic compounds constitute a vital role inorganic synthesis Here themagnetic nanoparticles are mod-ified with aminoacids such as cysteine and glutathione Bothaminoacids have highly reactive thiol group which can easilyfunctionalize the nanoferrite surface Of the two aminoacidsglutathione is superior to cysteine in reactivity The activesites of the nanocatalyst were left free for catalyzing the reac-tion This catalyst can be applied in the Paal-Knorr reactionsof pyrrole 2213 (Scheme 31) synthesis between variety ofamines 2211 and tetrahydro-25-dimethoxyfuran 2212Also this catalyst can be used in the synthesis of pyrazole2216 between 13-diketone 2214 and hydrazines 2215The entire reaction was carried out in toxic-free solvent(water) and effective microwave irradiation [115]


N Cl

CHO

N Cl

OH

22310 22311

(xxxviii)

(xxxviii) ZnO NaBH4 H2O RT

Scheme 35 ZnO nanoparticles mediated reduction of quinoline-3-carbaldehyde 22311

HN O

OCl RCl

N O

O

Cl

R

Cl

X

22312 2231422313

(xxxix)+

R =

X = CH3 OCH3

(xxxix) Ag DMSO 110∘C

Scheme 36 O-alkylation of quinoline 22314

222 Synthesis of Indole Synthesis of indole was carried outusing an innovative catalyst Pd supported on the cages ofMIL-101 [Cr

3F(H2O)2O(bdc)

3] This support is more water

soluble than the other inorganic supports Thereby thereactions in aqueous solution will be catalyzed effectivelyThe reaction between 2-iodoanilines 2221 and phenylacetylene 2222 in the presence of 3-PdMIL-101 will leadto the formation of indole 2223 (Scheme 32) In additionthe substituents on the ring will have an effect on the currentreaction medium [116]

223 Miscellaneous Functionalization on HeterocyclesParella and coworkers carried out the C-alkylation reaction(Scheme 33) of indoles 2231 with epoxide 2232 using themagnetic nano-Fe

3O4as a catalyst [117] Roopan and Khan

explored an efficient ligand-free cross-coupling reaction of2-chloro-3-(chloromethyl) benzo[h]quinoline 2236 withN-heterocycles such as piperidin-4-one 4(3H)-pyrimidoneand ethyl 6-chloro-12-dihydro-2-oxo-4-phenylquino-line-3-carboxylate using a catalytic amount of ZnO nanorodsas a recyclable catalyst to give its corresponding derivatives2237ndash2239 (Scheme 34) respectively [118] The possiblemechanism is described in Figure 4 The chloromethylderivative of quinoline 2236 is obtained from hydrox-ymethyl derivative 2235 which in turn is obtained fromaldehyde 2234 The reduction of 2-chloroquinoline-3-carbaldehydes 22310 into (2-chloroquinolin-3-yl)

methanol 22311 occurs using zinc oxide nanoparticles as acatalyst in an ecofriendly way (Scheme 35) [1] Roopan andcoworkers synthesized 1-2-[(2-chloroquinolin-3-yl) me-thoxy]-6-chloro-4phenylquinolin-3-yl ethanones 22314(Scheme 36) from heteroalkylhalides 22313 and cyclicamides 22312 using silver nanoparticles in regioselectiveO-alkylation reaction [119] Furthermore they have used Fenanoparticle for the regioselective N-alkylation of 4(3H)-pyrimidone 22317 (Scheme 37) with various quinolinecontaining alkyl halides in an ecofriendly way The possiblemechanism is described in Figure 5 [120]

3 Conclusions

This review is the first attempt to compile the literature onthe subject of nanomaterials application in organic synthesisIt should be noted that a correct and update citation andliterature survey is very important for researchers to findrelevant information pioneer ideas and progress of anysubject On the other hand published data using nanoma-terials indicate a wide synthetic potential of the describedcatalysts and a great interest of researchers in this fieldThe use of green nanocatalyst for the synthesis of variousheterocycles has advantages such as short reaction time highyield inexpensive chemicals usage easy work-up procedureand very specific reaction [2] The use of nanocatalyst canalso be applied on the synthesis of various heterocycles which


N

NH

N

Cl

Cl N

N

NCl

O

22315 22316 22317

O

(XL)

(XL) Fe KOH DMSO 110∘C

+

Scheme 37 Regioselective alkylation reaction towards pyrimidone molecule 22317

are very difficult to prepare by conventional methods Alsomore and transition metals can be checked for its catalyticactivity and surface modifications of the existing catalystcan also be performed In most of the reactions the spentcatalyst can be easily separated from the reaction mixturealso it can be reused without noticeable change in its catalyticactivity A wide range of original procedures for synthesizingvarious classes of organic compounds including organicfunctional group transformation have been developed on thebasis of nanoparticles We assume that the present reviewarticle may be bringing a basis to advance information to thisvery important subject and to encourage active researchersin this field for the synthesis of organic compounds usingnanoparticles

Acknowledgments

The authors thank the management of VIT University fortheir support and encouragement Furthermore the authorsthank their coworkers named in the references for theirexperimental and intellectual contributions

References

[1] S M Roopan and F R N Khan ldquoZnO nanoparticles in thesynthesis of AB ring core of camptothecinrdquo Chemical Papersvol 64 no 6 pp 812ndash817 2010

[2] G Madhumitha and S M Roopan ldquoDevastated crops multi-functional efficacy for the production of nanoparticlesrdquo Journalof Nanomaterials vol 2013 pp 1ndash12 2013

[3] L Sang-Bum P Young In D Mi-Sook and G Young-DaeldquoIdentification of 236-trisubstituted quinoxaline derivativesas a Wnt2120573-catenin pathway inhibitor in non-small-cell lungcancer cell linesrdquo Bioorganic ampMedicinal Chemistry Letters vol20 pp 5900ndash5904 2010

[4] N M Sabry H M Mohamed E S A E H Khattab S SMotlaq and A M El-Agrody ldquoSynthesis of 4119867-chromenecoumarin 12119867-chromeno[23-119889]pyrimidine derivatives andsome of their antimicrobial and cytotoxicity activitiesrdquo Euro-pean Journal of Medicinal Chemistry vol 46 no 2 pp 765ndash7722011

[5] R Raj P Singh P Singh J Gut P J Rosenthal and VKumar ldquoAzide-alkyne cycloaddition en route to 1H-123-triazole-tethered 7-chloroquinoline-isatin chimeras synthesisand antimalarial evaluationrdquo European Journal of MedicinalChemistry vol 62 pp 590ndash596 2013

[6] M M Sitonio C H Carvalho Jr I A Campos et al ldquoAnti-inflammatory and anti-arthritic activities of 3 4-dihydro-2 2-dimethyl-2119867-naphthol[12-119887]pyran-5 6-dione (120573-lapachone)rdquoInflammation Research vol 62 pp 107ndash113 2013

[7] R Ghorbani-Vaghei and S M Malaekehpoor ldquoN- Bromosuc-cinimide as an efficient catalyst for the synthesis of indolo [23-119887]quinolinesrdquo Tetrahedron Letters vol 53 pp 4751ndash4753 2012

[8] K Rad-Moghadam and S C Azimi ldquoMg(BF4)2doped in

[BMIm][BF4] a homogeneous ionic liquid-catalyst for effi-

cient synthesis of 1 8-dioxo-octahydroxanthenes decahy-droacridines and 14-aryl-14119867-dibenzo[a j]xanthenesrdquo Journalof Molecular Catalysis A vol 363-364 pp 465ndash469 2012

[9] T S Jin J C Xiao S J Wang and T S Li ldquoUltrasound-assistedsynthesis of 2-amino-2-chromenes with cetyltrimethylammo-nium bromide in aqueous mediardquo Ultrasonics Sonochemistryvol 11 no 6 pp 393ndash397 2004

[10] C L Ni X H Song H Yan X Q Song and R G ZhongldquoImproved synthesis of diethyl 26-dimethyl-4-aryl-4119867-pyran-35-dicarboxylate under ultrasound irradiationrdquo UltrasonicsSonochemistry vol 17 no 2 pp 367ndash369 2010

[11] G Chen H Jia L Zhang B Chen and J Li ldquoAn efficientsynthesis of 2-substituted benzothiazoles in the presence ofFeCl3Montmorillonite K-10 under ultrasound irradiationrdquo

Ultrasonics Sonochemistry vol 20 pp 627ndash632 2013[12] A LakMMazloumiM SMohajerani et al ldquoRapid formation

of mono-dispersed hydroxyapatite nanorods with narrow-sizedistribution viaMicrowave Irradiationrdquo Journal of the AmericanCeramic Society vol 91 no 11 pp 3580ndash3584 2008

[13] M S Mohajerani M Mazloumi A Lak A Kajbafvala SZanganeh and S K Sadrnezhaad ldquoSelf-assembled zinc oxidenanostructures via a rapidmicrowave-assisted routerdquo Journal ofCrystal Growth vol 310 no 15 pp 3621ndash3625 2008

[14] R Narayanan ldquoSynthesis of green nanocatalysts and industri-ally important green reactionsrdquo Green Chemistry Letters andReviews vol 5 pp 707ndash725 2012

[15] R M Mohamed D L McKinney and W M SigmundldquoEnhanced nanocatalystsrdquoMaterials Science and Engineering Rvol 73 pp 1ndash13 2012

[16] M Mazloumi N Shahcheraghi A Kajbafvala et al ldquo3Dbundles of self-assembled lanthanum hydroxide nanorods viaa rapid microwave-assisted routerdquo Journal of Alloys and Com-pounds vol 473 no 1-2 pp 283ndash287 2009

[17] A Kajbafvala H Ghorbani A Paravar J P Samberg EKajbafvala and S K Sadrnezhaad ldquoEffects of morphology onphotocatalytic performance of zinc oxide nanostructures syn-thesized by rapidmicrowave irradiationmethodsrdquo Superlatticesand Microstructures vol 51 pp 512ndash522 2012

[18] M R Bayati R Molaei A Kajbafvala S Zanganeh H RZargar and K Janghorban ldquoInvestigation on hydrophilicity


of micro-arc oxidized TiO2nanomicro-porous layersrdquo Elec-

trochimica Acta vol 55 no 20 pp 5786ndash5792 2010[19] A Kajbafvala J P Samberg H Ghorbani E Kajbafvala and

S K Sadrnezhaad ldquoEffects of initial precursor and microwaveirradiation on step-by-step synthesis of zinc oxide nano archi-tecturesrdquoMaterials Letters vol 67 pp 342ndash345 2012

[20] M Mazloumi S Zanganeh A Kajbafvala et al ldquoUltrasonicinduced photoluminescence decay in sonochemically obtainedcauliflower-like ZnO nanostructures with surface 1D nanoar-raysrdquo Ultrasonics Sonochemistry vol 16 no 1 pp 11ndash14 2009

[21] S Zanganeh A Kajbafvala N Zanganeh et al ldquoHydrothermalsynthesis and characterization of TiO

2nanostructures using

LiOH as a solventrdquo Advanced Powder Technology vol 22 no3 pp 336ndash339 2011

[22] A Kajbafvala S Zanganeh E Kajbafvala H R Zargar M RBayati and S K Sadrnezhaad ldquoMicrowave-assisted synthesisof narcis-like zinc oxide nanostructuresrdquo Journal of Alloys andCompounds vol 497 no 1-2 pp 325ndash329 2010

[23] A Kajbafvala M R Shayegh M Mazloumi et al ldquoNanostruc-ture sword-like ZnOwires rapid synthesis and characterizationthrough a microwave-assisted routerdquo Journal of Alloys andCompounds vol 469 no 1-2 pp 293ndash297 2009

[24] A Lak M Mazloumi M Mohajerani et al ldquoSelf-assembly ofdandelion-like hydroxyapatite nanostructures via hydrother-mal methodrdquo Journal of the American Ceramic Society vol 91no 10 pp 3292ndash3297 2008

[25] S Zanganeh A Kajbafvala N Zanganeh et al ldquoSelf-assemblyof boehmite nanopetals to form 3D high surface area nanoar-chitecturesrdquo Applied Physics A vol 99 no 1 pp 317ndash321 2010

[26] M Mazloumi M Attarchi A Lak et al ldquoBoehmite nanopetalsself assembled to form rosette-like nanostructuresrdquo MaterialsLetters vol 62 no 26 pp 4184ndash4186 2008

[27] S Zanganeh M Torabi A Kajbafvala et al ldquoCVD fabricationof carbon nanotubes on electrodeposited flower-like Fe nanos-tructuresrdquo Journal of Alloys and Compounds vol 507 no 2 pp494ndash497 2010

[28] Y Estevez M Quiliano A Burguete et al ldquoTrypanocidalproperties structure-activity relationship and computationalstudies of quinoxaline 14-di-119873-oxide derivativesrdquo Experimen-tal Parasitology vol 127 pp 745ndash751 2011

[29] E Vicente P R Duchowicz E A Castro and A MongeldquoQSAR analysis for quinoxaline-2-carboxylate 14-di-119873-oxidesas anti-mycobacterial agentsrdquo Journal ofMolecular Graphics andModelling vol 28 no 1 pp 28ndash36 2009

[30] H Yoo Y Lee M E Suh D J Kim and S W Park ldquoCytotoxiceffects of quinoxaline derivatives on human cancer cell linesrdquoArchiv Der Pharmazie vol 331 pp 331ndash333 1998

[31] M J Climent A Corma J C Hernandez A B HungrıaS Iborra and S Martınez-Silvestre ldquoBiomass into chemicalsone-pot two- and three-step synthesis of quinoxalines frombiomass-derived glycols and 12-dinitrobenzene derivativesusing supported gold nanoparticles as catalystsrdquo Journal ofCatalysis vol 292 pp 118ndash129 2012

[32] AHasaninejadM Shekouhy andA Zare ldquoSilica nanoparticlesefficiently catalyzed synthesis of quinolines and quinoxalinesrdquoCatalysis Science amp Technology vol 2 pp 201ndash214 2012

[33] B B FMirjalili A Bamoniri andA Akbari ldquoNano-BF3sdotSiO2 a

reusable and eco-friendly catalyst for synthesis of quinoxalinesrdquoChemistry of Heterocyclic Compounds vol 47 pp 487ndash491 2011

[34] B B F Mirjalili and A Akbari ldquoNano-TiO2 an eco-friendly

alternative for the synthesis of quinoxalinesrdquo Chinese ChemicalLetters vol 22 no 6 pp 753ndash756 2011

[35] H Y Lu S H Yang J Deng and Z H Zhang ldquoMagneticFe3O4nanoparticles as new efficient and reusable catalysts for

the synthesis of quinoxalines in waterrdquo Australian Journal ofChemistry vol 63 no 8 pp 1290ndash1296 2010

[36] A A Yelwande M E Navgire B R Arbad and M K LandeldquoPolyanilineSiO

2nanocomposite catalyzed efficient synthesis

of quinoxaline derivatives at room temperaturerdquo Journal of theChinese Chemical Society vol 59 pp 1ndash6 2012

[37] H Alinezhad M Tajbakhsh F Salehian and P BiparvaldquoSynthesis of quinoxaline derivatives using TiO

2nanoparticles

as an efficient and recyclable catalystrdquo Bulletin of the KoreanChemical Society vol 32 pp 3720ndash3725 2011

[38] A Kumar S kumar A Saxena A De and S MozumdarldquoNi-nanoparticles an efficient catalyst for the synthesis ofquinoxalinesrdquo Catalysis Communications vol 9 no 5 pp 778ndash784 2008

[39] G R Bardajee R Malakooti I Abtin and H AtashinldquoPalladium Schiff-base complex loaded SBA-15 as a novelnanocatalyst for the synthesis of 23-disubstituted quinoxalinesand pyridopyrazine derivativesrdquo Microporous and MesoporousMaterials vol 169 pp 67ndash74 2013

[40] B L Finkelstein and C J Strock ldquoSynthesis and insecticidalactivity of novel pyrazole methanesulfonatesrdquo Pesticide Sciencevol 50 no 4 pp 324ndash328 1997

[41] C M R De Santrsquoanna R B De Alencastro C R Rodrigueset al ldquoA semiempirical study of pyrazole acylhydrazones aspotential antimalarial agentsrdquo International Journal of QuantumChemistry vol 60 no 8 pp 1835ndash1843 1996

[42] A A Farghaly A A Bekhit and J Y Park ldquoDesign and synthe-sis of some oxadiazolyl thiadiazolyl thiazolidinyl and thiazolylderivatives of 1119867-pyrazole as anti-inflammatory antimicrobialagentsrdquo Archiv der Pharmazie vol 333 no 2-3 pp 53ndash57 2000

[43] F N Khan J S Jin T Maiyalagan et al ldquoIron-oxide nano-particles mediated cyclization of 3-(4-chlorophenyl)-1-hydraz-inylisoquinoline to 1-(45-dihydropyrazol-1-yl)isoquinolinesrdquoResearch on Chemical Intermediates vol 38 pp 571ndash582 2012

[44] S Rostamizadeh N Shadjou M Azad and N Jalali ldquo(120572-Fe2O3)-MCM-41 as a magnetically recoverable nanocatalyst for

the synthesis of pyrazolo[43-119888]pyridines at room temperaturerdquoCatalysis Communications vol 26 pp 218ndash224 2012

[45] J R Goodell A A Madhok H Hiasa and D M FergusonldquoSynthesis and evaluation of acridine- and acridone-based anti-herpes agents with topoisomerase activityrdquo Bioorganic andMedicinal Chemistry vol 14 no 16 pp 5467ndash5480 2006

[46] M Jones A E Mercer P A Stocks et al ldquoAntitumour and anti-malarial activity of artemisinin-acridine hybridsrdquo Bioorganicand Medicinal Chemistry Letters vol 19 no 7 pp 2033ndash20372009

[47] S M Roopan R Subashini A Bharathi G Rajakumar A ARahuman and P K Gullanki ldquoSynthesis spectral characteri-zation and larvicidal activity of acridin-1(2119867)-one analoguesrdquoSpectrochimica Acta A vol 95 pp 442ndash445 2012

[48] S M Roopan and F R N Khan ldquoSnO2nanoparticles medi-

ated nontraditional synthesis of biologically active 9-chloro-6 13-dihydro-7-phenyl-5119867-indolo[3 2-119888]-acridine derivativesrdquoMedicinal Chemistry Research vol 20 pp 732ndash737 2011

[49] M A Ghasemzadeh J Safaei-Ghomi and H Molaei ldquoFe3O4

nanoparticles as an efficient green and magnetically reusablecatalyst for the one-pot synthesis of 18-dioxo-decahydroa-cridine derivatives under solvent-free conditionsrdquo ComptesRendus Chimie vol 15 pp 969ndash974 2012


[50] S Rostamizadeh A Amirahmadi N Shadjou and A MAmani ldquoMCM-41-SO

3H as a nanoreactor for the one-pot

solvent-free synthesis of 1 8-dioxo-9-aryl decahydroacridinesrdquoJournal of Heterocyclic Chemistry vol 49 pp 111ndash115 2012

[51] A A Trabanco G Duvey J M Cid et al ldquoNew positiveallosteric modulators of the metabotropic glutamate receptor 2(mGluR2) identification and synthesis ofN-propyl-8-chloro-6-substituted isoquinolonesrdquo Bioorganic andMedicinal ChemistryLetters vol 21 no 3 pp 971ndash976 2011

[52] Y Asano S Kitamura T Ohra et al ldquoDiscovery synthesisand biological evaluation of isoquinolones as novel and highlyselective JNK inhibitorsrdquo Bioorganic and Medicinal Chemistryvol 16 no 8 pp 4699ndash4714 2008

[53] V Krishnakumar B K Mandal K M Kumar and F NKhan ldquoFlower-shaped ZnO nanoparticles as an efficientheterogeneous and reusable catalyst in the synthesis of N-arylhomophthalimides and benzannelated isoquinolinonesrdquoResearch on Chemical Intermediates vol 38 pp 1881ndash1892 2012

[54] B Japelj S Recnik P Cebasek B Stanovnik and J Svete ldquoSyn-thesis and antimycobacterial activity of alkyl 1-heteroaryl-1119867-123- triazole-4-carboxylatesrdquo Journal of Heterocyclic Chem-istry vol 42 no 6 pp 1167ndash1173 2005

[55] A K Jordao V F Ferreira T M L Souza et al ldquoSynthesis andanti-HSV-1 activity of new 123-triazole derivativesrdquo Bioorganicand Medicinal Chemistry vol 19 no 6 pp 1860ndash1865 2011

[56] N G Aher V S Pore N N Mishra et al ldquoSynthesis andantifungal activity of 123-triazole containing fluconazole ana-loguesrdquo Bioorganic and Medicinal Chemistry Letters vol 19 no3 pp 759ndash763 2009

[57] F Alonso Y Moglie G Radivoy and M Yus ldquoMulticompo-nent click synthesis of potentially biologically active triazolescatalysed by copper nanoparticles on activated carbon in waterrdquoHeterocycles vol 84 pp 1033ndash1044 2012

[58] J Albadi M Keshavarz F Shirini and M Vafaie-nezhadldquoCopper iodide nanoparticles on poly(4-vinyl pyridine) a newand efficient catalyst for multicomponent click synthesis of14-disubstituted-123-triazoles in waterrdquo Catalysis Communi-cations vol 27 pp 17ndash20 2012

[59] H Sharghi A Khoshnood M M Doroodmand and RKhalifeh ldquo14-Dihydroxyanthraquinone-copper(II) nanoparti-cles immobilized on silica gel a highly efficient copper scav-enger and recyclable heterogeneous nanocatalyst for a clickapproach to the three-component synthesis of 123-triazolederivatives inwaterrdquo Journal of the IranianChemical Society vol9 pp 231ndash250 2012

[60] B S P Anil Kumar K H V Reddy B Madhav K Ramesh andY V D Nageswar ldquoMagnetically separable CuFe

2O4nano par-

ticles catalyzed multicomponent synthesis of 14-disubstituted123-triazoles in tap water using lsquoclick chemistryrsquordquo TetrahedronLetters vol 53 pp 4595ndash4599 2012

[61] B Kaboudin Y Abedi and T Yokomatsu ldquoOne-pot synthesisof 123-triazoles from boronic acids in water using Cu(II)-120573-cyclodextrin complex as a nanocatalystrdquo Organic BiomolecularChemistry vol 10 pp 4543ndash4548 2012

[62] V Maddi K S Raghu and M N A Rao ldquoSynthesis and anti-inflammatory activity of 3-(benzylideneamino)coumarins inrodentsrdquo Journal of Pharmaceutical Sciences vol 81 no 9 pp964ndash965 1992

[63] M Roussaki C A Kontogiorgis D Hadjipavlou-Litina SHamilakis and A Detsi ldquoA novel synthesis of 3-aryl coumarinsand evaluation of their antioxidant and lipoxygenase inhibitory

activityrdquoBioorganic andMedicinal Chemistry Letters vol 20 no13 pp 3889ndash3892 2010

[64] S Sardari Y Mori K Horita R G Micetich S Nishibeand M Daneshtalab ldquoSynthesis and antifungal activity ofcoumarins and angular furanocoumarinsrdquo Bioorganic andMedicinal Chemistry vol 7 no 9 pp 1933ndash1940 1999

[65] B V Kumar H S B Naik D Girija and B V Kumar ldquoZnOnanoparticle as catalyst for efficient green one-pot synthesisof coumarins through Knoevenagel condensationrdquo Journal ofChemical Sciences vol 123 pp 615ndash621 2011

[66] I Manolov C Maichle-Moessmer I Nicolova and NDanchev ldquoSynthesis and anticoagulant activities of substituted24-diketochromans biscoumarins and chromanocoumarinsrdquoArchiv der Pharmazie vol 339 no 6 pp 319ndash326 2006

[67] J M Khurana and K Vij ldquoNickel nanoparticles a highlyefficient catalyst for one pot synthesis of tetraketones andbiscoumarinsrdquo Journal of Chemical Sciences vol 124 pp 907ndash912 2012

[68] Z Bouaziz J Riondal A Mey M Berlion J Villard andH Fillion ldquoSynthesis of some naphthoxazine carbolactonederivatives with in vitro cytotoxic and antifungal activitiesrdquoEuropean Journal ofMedicinal Chemistry vol 26 no 4 pp 469ndash472 1991

[69] A Kumar A Saxena M Dewan A De and S Mozum-dar ldquoRecyclable nanoparticulate copper mediated synthesis ofnaphthoxazinones in PEG-400 a green approachrdquo TetrahedronLetters vol 52 pp 4835ndash4839 2011

[70] G A M Nawwar ldquoSalicylamides containing amino acid orpyran moieties with molluscicidal activityrdquo Archiv der Phar-mazie vol 327 no 4 pp 201ndash205 1994

[71] A Plant A Harder N Mencke and H Bertram ldquoSynthesisand anthelmintic activity of 7-hydroxy- 5-oxo-5119867-thieno[32-119887]pyran-6-carboxanilides and -6-thiocarboxanilidesrdquo PestManagement Science vol 48 pp 351ndash358 1996

[72] N Babakhani and S Keshipoor ldquoTiO2and TiO

2nanoparticles

as efficient and recoverable catalysts for the synthesis of pyranannulated heterocyclic systemsrdquo Research on Chemical Interme-diates 2012

[73] H Mehrabi and M Kazemi-Mireki ldquoCuO nanoparticles anefficient and recyclable nanocatalyst for the rapid and greensynthesis of 34-dihydropyrano[119888]chromenesrdquo Chinese Chemi-cal Letters vol 22 pp 1419ndash1422 2011

[74] M Khoobi L Marsquomani F Rezazadeh et al ldquoOne-pot synthesisof 4119867-benzo[119887]pyrans and dihydropyrano[119888]chromenes usinginorganic-organic hybridmagnetic nanocatalyst in waterrdquo Jour-nal of Molecular Catalysis A vol 359 pp 74ndash80 2012

[75] S Rostamizadeh N Shadjou andM Hasanzadeh ldquoApplicationof MCM-41-SO

3H as an advanced nanocatalyst for the solvent

free synthesis of pyrano[3 2-119888]pyridine derivativesrdquo Journal ofthe Chinese Chemical Society vol 59 pp 866ndash871 2012

[76] H Valizadeh and A A Azimi ldquoZnOMgO containing ZnOnanoparticles as a highly effective heterogeneous base catalystfor the synthesis of 4119867-pyrans and coumarins in [bmim]BF

4rdquo

Journal of the Iranian Chemical Society vol 8 no 1 pp 123ndash1302011

[77] H Nagabhushana S Sandeep Saundalkar L Muralidhar et alldquo120572-Fe

2O3nanoparticles an efficient inexpensive catalyst for

the one-pot preparation of 34-dihydropyrano[119888] chromenesrdquoChinese Chemical Letters vol 22 no 2 pp 143ndash146 2011

[78] M Hosseini R Miri M Amini et al ldquoSynthesis QSAR andcalcium channel antagonist activity of new 14-dihydropyridine


derivatives containing 1-methy 1-45-dichloroimidazolyl sub-stituentsrdquo Archiv der Pharmazie vol 340 no 10 pp 549ndash5562007

[79] I Kruk A Kladna K Lichszteld et al ldquoAntioxidant activityof 4-flavonil-14-dihydropyridine derivativesrdquo Biopolymers vol62 no 3 pp 163ndash167 2001

[80] R Murugan K Ramamoorthy S Sundarrajan and S Ramakr-ishna ldquoMagnesium oxide nanotubes synthesis characteriza-tion and application as efficient recyclable catalyst for pyrazolyl14-dihydropyridine derivativesrdquo Tetrahedron vol 68 pp 7196ndash7201 2012

[81] C Y Fiakpui O A Phillips K S K Murthy and E EKnaus ldquoSynthesis and anticonvulsant activities of 5-(2-Chlo-rophenyl)7119867-pyrido [43-119891] [124]triazolo [43-119886] [14]diazep-inesrdquo Journal of Heterocyclic Chemistry vol 36 no 2 pp 377ndash380 1999

[82] R Ramajayam R Giridhar M R Yadav et al ldquoSynthe-sis antileukemic and antiplatelet activities of 23-diaryl-67-dihydro-5119867-14-diazepinesrdquo European Journal of MedicinalChemistry vol 43 no 9 pp 2004ndash2010 2008

[83] A Maleki ldquoFe3O4SiO2nanoparticles an efficient and magnet-

ically recoverable nanocatalyst for the one-potmulticomponentsynthesis of diazepinesrdquo Tetrahedron vol 68 pp 7827ndash78332012

[84] E Lukevics L Lgnatovich I Sleiksha et al ldquoSynthesis struc-ture and cytotoxic activity of 2-acetyl-5- trimethylsilylthio-phene(furan) and their oximesrdquo Applied Organometallic Chem-istry vol 20 no 7 pp 454ndash458 2006

[85] A Foroumadi N Mohammadhosseini S Emami et al ldquoSyn-thesis and antibacterial activity of new 7-piperazinylquinolonescontaining a functionalized 2-(furan-3-yl)ethyl moietyrdquo Archivder Pharmazie vol 340 no 1 pp 47ndash52 2007

[86] J Safaei-Ghomi M A Ghasemzadeh and A Kakavand-Qalenoei ldquoCuI-nanoparticles-catalyzed one-pot synthesis ofbenzo[119887]furans via three-component coupling of aldehydesamines and alkynerdquo Journal of Saudi Chemical Society 2012

[87] N Mulakayala P V N S Murthy D Rambabu et alldquoCatalysis by molecular iodine a rapid synthesis of 18-dioxo-octahydroxanthenes and their evaluation as potential anti-cancer agentsrdquo Bioorganic amp Medicinal Chemistry Letters vol22 pp 2186ndash2191 2012

[88] S Rostamizadeh A M Amani G H Mahdavinia G Amiriand H Sepehrian ldquoUltrasound promoted rapid and greensynthesis of 18-dioxo-octahydroxanthenes derivatives usingnanosized MCM-41-SO

3H as a nanoreactor nanocatalyst in

aqueous mediardquo Ultrasonics Sonochemistry vol 17 no 2 pp306ndash309 2010

[89] I Banti S Nencetti E Orlandini A Lapucci M C Breschiand S Fogli ldquoSynthesis and in-vitro antitumour activity of newnaphthyridine derivatives on human pancreatic cancer cellsrdquoJournal of Pharmacy and Pharmacology vol 61 no 8 pp 1057ndash1066 2009

[90] P M Sivakumar G Iyer and M Doble ldquoQSAR studies onsubstituted 3- or 4-phenyl-18-naphthyridine derivatives asantimicrobial agentsrdquoMedicinal Chemistry Research vol 21 pp788ndash795 2012

[91] S Rostamizadeh M Azad N Shadjou and M Hasanzadehldquo(120572-Fe

2O3)-MCM-41-SO

3H as a novel magnetic nanocatalyst

for the synthesis of N-aryl-2-amino-1 6-naphthyridine deriva-tivesrdquo Catalysis Communications vol 25 pp 83ndash91 2012

[92] A Dandia V Parewa and K S Rathore ldquoSynthesis andcharacterization of CdS and Mn doped CdS nanoparticles

and their catalytic application for chemoselective synthesisof benzimidazoles and benzothiazoles in aqueous mediumrdquoCatalysis Communications vol 28 pp 90ndash94 2012

[93] P Gupta S Hameed and R Jain ldquoRing-substituted imidazolesas a new class of anti-tuberculosis agentsrdquo European Journal ofMedicinal Chemistry vol 39 no 9 pp 805ndash814 2004

[94] A Khalafi-Nezhad M N Soltani Rad H Mohabatkar ZAsrari andBHemmateenejad ldquoDesign synthesis antibacterialand QSAR studies of benzimidazole and imidazole chloroary-loxyalkyl derivativesrdquo Bioorganic and Medicinal Chemistry vol13 no 6 pp 1931ndash1938 2005

[95] H Zang Q Su Y Mo B W Cheng and S Jun ldquoIonic liquid[EMIM]OAc under ultrasonic irradiation towards the first syn-thesis of trisubstituted imidazolesrdquo Ultrasonics Sonochemistryvol 17 no 5 pp 749ndash751 2010

[96] M V Chary N C Keerthysri S V N Vupallapati N Lingaiahand S Kantevari ldquoTetrabutylammonium bromide (TBAB) inisopropanol an efficient novel neutral and recyclable catalyticsystem for the synthesis of 245-trisubstituted imidazolesrdquoCatalysis Communications vol 9 no 10 pp 2013ndash2017 2008

[97] S Kantevari S V N Vuppalapati D O Biradar and LNagarapu ldquoHighly efficient one-pot solvent-free synthesis oftetrasubstituted imidazoles using HClO

4-SiO2as novel hetero-

geneous catalystrdquo Journal of Molecular Catalysis A vol 266 no1-2 pp 109ndash113 2007

[98] B F Mirjalili A H Bamoniri and L Zamani ldquoOne-potsynthesis of 1245-tetrasubstituted imidazoles promoted bynano-TiCl

4SiO2rdquo Scientia Iranica Transactions C vol 19 pp

565ndash568 2012[99] G M Ziarani A Badiei N Lashgari and Z Farahani

ldquoEfficient one-pot synthesis of 245-trisubstituted and 1245-tetrasubstituted imidazoles using SBA-Pr-SO

3Has a green nano

catalystrdquo Journal of Saudi Chemical Society 2013[100] J Safari S Gandomi-Ravandi and Z Akbari ldquoSonochemical

synthesis of 1245-tetrasubstituted imidazoles using nanocrys-talline MgAl

2O4as an effective catalystrdquo Journal of Advanced

Research 2012[101] A Teimouri and A N Chermahini ldquoAn efficient and one-

pot synthesis of 245-trisubstituted and 1245-tetrasubstitutedimidazoles catalyzed via solid acid nano-catalystrdquo Journal ofMolecular Catalysis A vol 346 pp 39ndash45 2011

[102] M G Hossein A A Mohammad and S Hamid ldquoMCM-41-SO3H as a highly efficient sulfonic acid nanoreactor for the

rapid and green synthesis of some novel highly substitutedimidazoles under solvent-free conditionrdquo Chinese Journal ofChemistry vol 30 pp 703ndash708 2012

[103] B Karami K Eskandari and A Ghasemi ldquoFacile and rapidsynthesis of some novel polysubstituted imidazoles by employ-ing magnetic Fe

3O4nanoparticles as a high efficient catalystrdquo

Turkish Journal of Chemistry vol 36 pp 601ndash614 2012[104] S J Ahmadi M Hosseinpour and S Sadjadi ldquoGranulated

copper oxide nanocatalyst a mild and efficient reusable catalystfor the one-pot synthesis of 4-amino-5-pyrimidinecarbonitrilesunder aqueous conditionsrdquoMonatshefte furChemie vol 142 pp1163ndash1168 2011

[105] R Hekmatshoar G N Kenary S Sadjadi and Y S BeheshtihaldquoZnO Nanoparticles a mild and efficient reusable catalyst forthe one-pot synthesis of 4-amino-5-pyrimidinecarbonitrilesunder aqueous conditionsrdquo Synthetic Communications vol 40no 13 pp 2007ndash2013 2010

[106] MM Heravi S Sadjadi S Sadjadi H A Oskooie R H Shoarand F F Bamoharram ldquoSupported preyssler nanoparticles in


synthesis of 13-diaryl-5- spirohexahydropyrimidinesrdquo Journalof the Chinese Chemical Society vol 56 no 2 pp 246ndash250 2009

[107] B W J Chen L L Chng J Yang Y Wei J Yang and J YYing ldquoPalladium-based nanocatalyst for one-pot synthesis ofpolysubstituted quinolinesrdquoChemCatChem vol 5 pp 277ndash2832013

[108] S J Ahmadi M Hosseinpour and S Sadjadi ldquoNanocrystallinecopper(II) oxide-catalyzed one-pot synthesis of imidazo[12-119886 ]quinoline and quinolino[12-119886 ]quinazoline derivatives viaa three-component condensationrdquo Synthetic Communicationsvol 41 no 3 pp 426ndash435 2011

[109] H R Prakash Naik H S Bhojya Naik T R RavikumarNaik T Aravinda and D S Lamani ldquoTiO

2nanopow-

der catalyzed microwave-induced one-pot synthesis of novelquinolinebenzo[ℎ]quinoline3-carbonitrile under solvent freeconditionsrdquo Phosphorus Sulfur and Silicon and the RelatedElements vol 184 no 8 pp 2109ndash2114 2009

[110] J M Nezhad J Akbari A Heydari and B Alirezapour ldquoCuOnanoparticles as an efficient and reusable catalyst for the one-pot Friedlander quinoline synthesisrdquo Bulletin of the KoreanChemical Society vol 32 pp 3853ndash3854 2011

[111] M So Y Liu C Ho K Lam and C Che ldquoSilica-supportedgold nanoparticles catalyzed one-pot tandem aerobic oxidativecyclization reaction for nitrogen-containing polyheterocycliccompoundsrdquo ChemCatChem vol 3 pp 386ndash393 2011

[112] M B Gawande A Velhinho I D Nogueira C A A Ghum-man O M N D Teodoro and P S Branco ldquoA facile synthesisof cysteine-ferrite magnetic nanoparticles for application inmulticomponent reactionsmdasha sustainable protocolrdquo The RoyalSociety of Chemistry vol 2 pp 6144ndash6149 2012

[113] S Abdolmohammadi ldquoTiO2nanoparticles as an effective cata-

lyst for the synthesis of hexahydro-2-quinolinecarboxylic acidsderivativesrdquo Chinese Chemical Letters vol 23 pp 1003ndash10062012

[114] S Sadjadi R Hekmatshoar S J Ahmadi M Hosseinpour andM Outokesh ldquoOn water a practical and efficient synthesisof benzoheterocycle derivatives catalyzed by nanocrystallinecopper(II) oxiderdquo Synthetic Communications vol 40 no 4 pp607ndash614 2010

[115] V Polshettiwar and R S Varma ldquoNano-organocatalyst mag-netically retrievable ferrite-anchored glutathione for micro-wave-assisted Paal-Knorr reaction aza-Michael addition andpyrazole synthesisrdquo Tetrahedron vol 66 no 5 pp 1091ndash10972010

[116] H Li Z Zhu F Zhang et al ldquoPalladium nanoparticles confinedin the cages of MIL-101 an efficient catalyst for the one-potindole synthesis in waterrdquo ACS Catalysis vol 1 pp 1604ndash16122011

[117] R Parella Naveen and S A Babu ldquoMagnetic nano Fe3O4

and CuFe2O4as heterogeneous catalysts a green method

for the stereo- and regioselective reactions of epoxides withindolespyrrolesrdquo Catalysis Communications vol 29 pp 118ndash121 2012

[118] S M Roopan and F R N Khan ldquoZnO nanorods catalyzedN-alkylation of piperidin-4-one 4(3H)-pyrimidone and ethyl6-chloro-12-dihydro-2-oxo-4-phenylquinoline-3-carboxylaterdquoChemical Papers vol 64 no 5 pp 678ndash682 2010

[119] S M Roopan M Gund F N Khan R Kumar J S Jin andA S Kumar ldquoRegioselective O-alkylation synthesis of 1-2-[(2chloroquinolin-3-yl)methoxy]-6-chloro-4phenylquinolin-3-ylethanonesrdquo Research on Chemical Intermediates vol 38 pp1111ndash1118 2012

[120] S M Roopan F R N Khan and B K Mandal ldquoFe nanoparticles mediated CndashN bond-forming reaction regioselec-tive synthesis of 3-[(2-chloroquinolin-3-yl)methyl]pyrimidin-4(3119867)onesrdquo Tetrahedron Letters vol 51 no 17 pp 2309ndash23112010

Submit your manuscripts athttpwwwhindawicom

ScientificaHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

CorrosionInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Polymer ScienceInternational Journal of



CeramicsJournal of


CompositesJournal of

NanoparticlesJournal of



International Journal of

Biomaterials


NanoscienceJournal of

TextilesHindawi Publishing Corporation httpwwwhindawicom Volume 2014

Journal of

NanotechnologyHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

CrystallographyJournal of


The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014


CoatingsJournal of

Advances in

Materials Science and EngineeringHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Smart Materials Research



MetallurgyJournal of


BioMed Research International

MaterialsJournal of


Nano

materials


Journal ofNanomaterials


Application of

nanoparticles

Quinoxaline

Pyrazole Acridine

Isoquinolinones

123-Triazoles

Coumarins

Naphthoxazinones

Pyran Pyridine

Diazepines

Xanthene

Quinoline

Miscellaneousreaction

Benzo[b]furance

Figure 1 Application of nanoparticles in organic synthesis

NH2R

minusH2O

Figure 2 Possible mechanism for the formation of N-arylhomophthalimide 242

O O

S

NNH

NO

Anti-inflammatory

(a)

O O

S

NN

Antiallergic

O

Cl

(b)

O O

S

NN CH

Anticoagulant

(c)

O O

Antitumor

ONH

NR

O

(d)

Figure 3 Pharmacological activities of coumarins


N

Cl

Cl

ZnO nanorod

NH

O

N

O

KCl

N Cl

N

O+ KOH

K+

+ H2O

+


N

N

O

N

N

O

N

N

O

N

Cl

Cl

N

N

O

N Cl

KOH

Fe nanoparticle

minus

minus

KCl + H2O

















3O4








2atmosphere





3O4







3O4 CuO





O

O N

N

Ph

Ph

(i)

NH2

NH2


+

211 212 213


NCl

N

N

Cl

N

O

222221 223

(ii)

H2NHN

+



N

O

225a

225b

225c224

N

N

226

NR

(iii)

NHNH2

NHNH2 Ac2O

CH3NHNH2



Cl O

HN

O

N

HN

Cl

(iv)

231 232 233

NH2

+




O

O

O

(v)

(vi)

NH

O O

236

N

O OPh

237

234 235


+

C6H5


(vii)

(viii)241

COOH

COOH

N

O

O

N

O

X

242

243



X = O S NH









251

O

252

Br

253O

Br

254

255

O

256

BHO

HO

257

NN

N

R258

Na+NminusminusN

R1

N+

Phenacyl bromide254


azide 251

Styrene oxide256

sodium azide251 and

phenylacetylene255



azide 251



255

123-

triazole



255


OH

O

+ O

OEtO O

261 262 263

(ix)

R1

R1

R2

R3

R3 R4

R2

R4



H OH OMe Et2N








O O OO O

OH R OH

O

OH

(x)

271 272 273

RCHO+


piperonyl


OO HO

(xi)O

HNO

281 282 283284

H2N NH2

++



NC CN (xii)

291 292

O

O

RNC CN

293

O

R

O

NC CNCN

NH2

+



NC CN

294 295

(xiii)(xiv)(xv)

(xvi)

O

OArNC

EtOOC

298

O

CNAr

EtOOC

2911

299

O

O

O

Ar

CN

2910

H3C

NH2

NH2



+

COCH3

H2N

PhndashCHO



N

O

2912

N

O

2913

NC CN

295

(xvii)

CN


+

NH2


NN

CHOMeO OMe

O O

N N

NH

Cl

Me Me

Cl

(xviii)

2101

2102

2103 2104

AcONH4

+

+

MeO2C CO2Me



O

NH

HN O

2111 2112 2113 2114(xix)

H2N NH2

R2

R2

R2

R3

R3

R3

+ +R1

R1

R4

R1 =


R4ndashNC



CHO

OH

O

Ph

NH

O N

O

2121 2122 2123 2124

(xx)


+ +



CHO

O

OO

2131 2133

(xxi)

O

O

2132

NO2

NO2

+



N

OCN

CN

N

N

NHCN

2141 2142 2143 2144

(xxii)Cl Cl

Cl Cl

+ +

NH2

(xxii) 120572-Fe2O

3-MCM-41-SO






4 CuCl

2 Cu (NO









XH(xxiii)

CHON

XR

NH2

+ R1

X = N 2151X = S 2152

R1 = 2153


∘C

X = NH 2154

R1 = Cl NO2 Me OMe

X = S 2155


O

O

Ph

Ph

2161

CHO

2162 2163

(xxiv)

NN

PhPh

2164

+ + NH2








2and TiO

2nanoparticles as







2O3nanopowder








NC CN

NH

N

N

R

CN

CHO

X2171 2172 2173

2174

(xxv)+ + NH2

NH2

R998400

R998400

R998400

= Ph NH2



O

R

N

NOAr

Ar

R

O

2181 2 182 2183 2184

(xxvi)+ + Ar-NH2

R = H CH3












2O3)-MCM-





OH

N

O OBase argon

2191 2192 2193

2195

OH

2194

(xxvii)

R1 R1

R1

+

+

R2R2

R2

R3

R3

R1 = R2 = Ph 234-MeC6H4 4-OMeC6 3C6H4


NH2

H4 4-CF


O

NH

COOH

NC CN N

OCN

NH

O

N

OCN

NH

O

O

NH

COOH

2196 2197

21982199

21910

21911

(xxviii)(xxviii)R1

R1R1

CHO +






4-





2O4


CHO

+NC

OO

2196 21912

(xxix)

N

CN

OH

21914

N

CN

OH

21915

21913R1

R1

NH2

NH2

(xxix) TiO2NPs MW


O

R X

N

R

X

O O

N

RO

O

21917

21916

21918

2191921920

(xxx) (xxx)NH2

R1

R2

R1

R2

R1 = R2 = H CH3




3H was


3O4nanoparticles






3CN




H N

O

(xxxi)

21913 2196 21921

+

NH2

R2

R2

R2

R1R1




O

O

+OHC

O

OO

NH

O

O

O(xxxii)

21918 21922 2162 21923

21924


OCH2Ph

OCH2Ph

OCH2Ph

OCH2Ph+ +NH4OAC







2-



2








O

O

OH

O

O

NH

O

COOH21925 21926

21927

R1

R1

R2

R2

R2

R2

NH4OAc

R1 = Cl OCH3

R2 = H Me

+ +

CH3

TiO2 NPs


Y

XH

Y

X

HN O

2201 2202 2203

(xxxiii)


NH2

+ RO2C CO2R

CO2R

X = S O NHR = CH3

Y = CH N C2H5


O OMeMeON

R

R

O O

X

+N

N

X(xxxiv)

2211 22122213

2214 2215 2216

(xxxiv)


NH2

+


NHNH2

X = H Et ClR1

R1

= MemiddotOEt


INHR

R

2221 22222223

(xxxv)

(xxxv) 3 PdMIL-101

NH2

+



2231 2232

2233

N

O

N

OH

(xxxvi)


R1

R1

R2

R2

R3

R4

R4

R3

R5

R5


R4 = H Et


R6

R6

R7

R7

+


R OR

OHR

Cl

N

N

O

N O

a

b

c

R

R

N

OEt

R

O

O

Cl

(xxxvii)2234 2235 2236

2237

2238

2239N Cl N Cl

NaBH4 SOCl2


R =










N Cl

CHO

N Cl

OH

22310 22311

(xxxviii)



HN O

OCl RCl

N O

O

Cl

R

Cl

X

22312 2231422313

(xxxix)+

R =

X = CH3 OCH3




3F(H2O)2O(bdc)







3 Conclusions



N

NH

N

Cl

Cl N

N

NCl

O

22315 22316 22317

O

(XL)


+



Acknowledgments


References



















































2nanoparticles































2O4nano par-















2nanoparticles








4rdquo
























2O3)-MCM-41-SO
















3Has a green nano



















2nanopow-























CeramicsJournal of







Biomaterials




Journal of


Journal of





CoatingsJournal of

Advances in








MaterialsJournal of


Nano

materials




N

Cl

Cl

ZnO nanorod

NH

O

N

O

KCl

N Cl

N

O+ KOH

K+

+ H2O

+


N

N

O

N

N

O

N

N

O

N

Cl

Cl

N

N

O

N Cl

KOH

Fe nanoparticle

minus

minus

KCl + H2O

















3O4








2atmosphere





3O4







3O4 CuO





O

O N

N

Ph

Ph

(i)

NH2

NH2


+

211 212 213


NCl

N

N

Cl

N

O

222221 223

(ii)

H2NHN

+



N

O

225a

225b

225c224

N

N

226

NR

(iii)

NHNH2

NHNH2 Ac2O

CH3NHNH2



Cl O

HN

O

N

HN

Cl

(iv)

231 232 233

NH2

+




O

O

O

(v)

(vi)

NH

O O

236

N

O OPh

237

234 235


+

C6H5


(vii)

(viii)241

COOH

COOH

N

O

O

N

O

X

242

243



X = O S NH









251

O

252

Br

253O

Br

254

255

O

256

BHO

HO

257

NN

N

R258

Na+NminusminusN

R1

N+

Phenacyl bromide254


azide 251

Styrene oxide256

sodium azide251 and

phenylacetylene255



azide 251



255

123-

triazole



255


OH

O

+ O

OEtO O

261 262 263

(ix)

R1

R1

R2

R3

R3 R4

R2

R4



H OH OMe Et2N








O O OO O

OH R OH

O

OH

(x)

271 272 273

RCHO+


piperonyl


OO HO

(xi)O

HNO

281 282 283284

H2N NH2

++



NC CN (xii)

291 292

O

O

RNC CN

293

O

R

O

NC CNCN

NH2

+



NC CN

294 295

(xiii)(xiv)(xv)

(xvi)

O

OArNC

EtOOC

298

O

CNAr

EtOOC

2911

299

O

O

O

Ar

CN

2910

H3C

NH2

NH2



+

COCH3

H2N

PhndashCHO



N

O

2912

N

O

2913

NC CN

295

(xvii)

CN


+

NH2


NN

CHOMeO OMe

O O

N N

NH

Cl

Me Me

Cl

(xviii)

2101

2102

2103 2104

AcONH4

+

+

MeO2C CO2Me



O

NH

HN O

2111 2112 2113 2114(xix)

H2N NH2

R2

R2

R2

R3

R3

R3

+ +R1

R1

R4

R1 =


R4ndashNC



CHO

OH

O

Ph

NH

O N

O

2121 2122 2123 2124

(xx)


+ +



CHO

O

OO

2131 2133

(xxi)

O

O

2132

NO2

NO2

+



N

OCN

CN

N

N

NHCN

2141 2142 2143 2144

(xxii)Cl Cl

Cl Cl

+ +

NH2

(xxii) 120572-Fe2O

3-MCM-41-SO






4 CuCl

2 Cu (NO









XH(xxiii)

CHON

XR

NH2

+ R1

X = N 2151X = S 2152

R1 = 2153


∘C

X = NH 2154

R1 = Cl NO2 Me OMe

X = S 2155


O

O

Ph

Ph

2161

CHO

2162 2163

(xxiv)

NN

PhPh

2164

+ + NH2








2and TiO

2nanoparticles as







2O3nanopowder








NC CN

NH

N

N

R

CN

CHO

X2171 2172 2173

2174

(xxv)+ + NH2

NH2

R998400

R998400

R998400

= Ph NH2



O

R

N

NOAr

Ar

R

O

2181 2 182 2183 2184

(xxvi)+ + Ar-NH2

R = H CH3












2O3)-MCM-





OH

N

O OBase argon

2191 2192 2193

2195

OH

2194

(xxvii)

R1 R1

R1

+

+

R2R2

R2

R3

R3

R1 = R2 = Ph 234-MeC6H4 4-OMeC6 3C6H4


NH2

H4 4-CF


O

NH

COOH

NC CN N

OCN

NH

O

N

OCN

NH

O

O

NH

COOH

2196 2197

21982199

21910

21911

(xxviii)(xxviii)R1

R1R1

CHO +






4-





2O4


CHO

+NC

OO

2196 21912

(xxix)

N

CN

OH

21914

N

CN

OH

21915

21913R1

R1

NH2

NH2

(xxix) TiO2NPs MW


O

R X

N

R

X

O O

N

RO

O

21917

21916

21918

2191921920

(xxx) (xxx)NH2

R1

R2

R1

R2

R1 = R2 = H CH3




3H was


3O4nanoparticles






3CN




H N

O

(xxxi)

21913 2196 21921

+

NH2

R2

R2

R2

R1R1




O

O

+OHC

O

OO

NH

O

O

O(xxxii)

21918 21922 2162 21923

21924


OCH2Ph

OCH2Ph

OCH2Ph

OCH2Ph+ +NH4OAC







2-



2








O

O

OH

O

O

NH

O

COOH21925 21926

21927

R1

R1

R2

R2

R2

R2

NH4OAc

R1 = Cl OCH3

R2 = H Me

+ +

CH3

TiO2 NPs


Y

XH

Y

X

HN O

2201 2202 2203

(xxxiii)


NH2

+ RO2C CO2R

CO2R

X = S O NHR = CH3

Y = CH N C2H5


O OMeMeON

R

R

O O

X

+N

N

X(xxxiv)

2211 22122213

2214 2215 2216

(xxxiv)


NH2

+


NHNH2

X = H Et ClR1

R1

= MemiddotOEt


INHR

R

2221 22222223

(xxxv)

(xxxv) 3 PdMIL-101

NH2

+



2231 2232

2233

N

O

N

OH

(xxxvi)


R1

R1

R2

R2

R3

R4

R4

R3

R5

R5


R4 = H Et


R6

R6

R7

R7

+


R OR

OHR

Cl

N

N

O

N O

a

b

c

R

R

N

OEt

R

O

O

Cl

(xxxvii)2234 2235 2236

2237

2238

2239N Cl N Cl

NaBH4 SOCl2


R =










N Cl

CHO

N Cl

OH

22310 22311

(xxxviii)



HN O

OCl RCl

N O

O

Cl

R

Cl

X

22312 2231422313

(xxxix)+

R =

X = CH3 OCH3




3F(H2O)2O(bdc)







3 Conclusions



N

NH

N

Cl

Cl N

N

NCl

O

22315 22316 22317

O

(XL)


+



Acknowledgments


References



















































2nanoparticles































2O4nano par-















2nanoparticles








4rdquo
























2O3)-MCM-41-SO
















3Has a green nano



















2nanopow-























CeramicsJournal of







Biomaterials




Journal of


Journal of





CoatingsJournal of

Advances in








MaterialsJournal of


Nano

materials
















3O4








2atmosphere





3O4







3O4 CuO





O

O N

N

Ph

Ph

(i)

NH2

NH2


+

211 212 213


NCl

N

N

Cl

N

O

222221 223

(ii)

H2NHN

+



N

O

225a

225b

225c224

N

N

226

NR

(iii)

NHNH2

NHNH2 Ac2O

CH3NHNH2



Cl O

HN

O

N

HN

Cl

(iv)

231 232 233

NH2

+




O

O

O

(v)

(vi)

NH

O O

236

N

O OPh

237

234 235


+

C6H5


(vii)

(viii)241

COOH

COOH

N

O

O

N

O

X

242

243



X = O S NH









251

O

252

Br

253O

Br

254

255

O

256

BHO

HO

257

NN

N

R258

Na+NminusminusN

R1

N+

Phenacyl bromide254


azide 251

Styrene oxide256

sodium azide251 and

phenylacetylene255



azide 251



255

123-

triazole



255


OH

O

+ O

OEtO O

261 262 263

(ix)

R1

R1

R2

R3

R3 R4

R2

R4



H OH OMe Et2N








O O OO O

OH R OH

O

OH

(x)

271 272 273

RCHO+


piperonyl


OO HO

(xi)O

HNO

281 282 283284

H2N NH2

++



NC CN (xii)

291 292

O

O

RNC CN

293

O

R

O

NC CNCN

NH2

+



NC CN

294 295

(xiii)(xiv)(xv)

(xvi)

O

OArNC

EtOOC

298

O

CNAr

EtOOC

2911

299

O

O

O

Ar

CN

2910

H3C

NH2

NH2



+

COCH3

H2N

PhndashCHO



N

O

2912

N

O

2913

NC CN

295

(xvii)

CN


+

NH2


NN

CHOMeO OMe

O O

N N

NH

Cl

Me Me

Cl

(xviii)

2101

2102

2103 2104

AcONH4

+

+

MeO2C CO2Me



O

NH

HN O

2111 2112 2113 2114(xix)

H2N NH2

R2

R2

R2

R3

R3

R3

+ +R1

R1

R4

R1 =


R4ndashNC



CHO

OH

O

Ph

NH

O N

O

2121 2122 2123 2124

(xx)


+ +



CHO

O

OO

2131 2133

(xxi)

O

O

2132

NO2

NO2

+



N

OCN

CN

N

N

NHCN

2141 2142 2143 2144

(xxii)Cl Cl

Cl Cl

+ +

NH2

(xxii) 120572-Fe2O

3-MCM-41-SO






4 CuCl

2 Cu (NO









XH(xxiii)

CHON

XR

NH2

+ R1

X = N 2151X = S 2152

R1 = 2153


∘C

X = NH 2154

R1 = Cl NO2 Me OMe

X = S 2155


O

O

Ph

Ph

2161

CHO

2162 2163

(xxiv)

NN

PhPh

2164

+ + NH2








2and TiO

2nanoparticles as







2O3nanopowder








NC CN

NH

N

N

R

CN

CHO

X2171 2172 2173

2174

(xxv)+ + NH2

NH2

R998400

R998400

R998400

= Ph NH2



O

R

N

NOAr

Ar

R

O

2181 2 182 2183 2184

(xxvi)+ + Ar-NH2

R = H CH3












2O3)-MCM-





OH

N

O OBase argon

2191 2192 2193

2195

OH

2194

(xxvii)

R1 R1

R1

+

+

R2R2

R2

R3

R3

R1 = R2 = Ph 234-MeC6H4 4-OMeC6 3C6H4


NH2

H4 4-CF


O

NH

COOH

NC CN N

OCN

NH

O

N

OCN

NH

O

O

NH

COOH

2196 2197

21982199

21910

21911

(xxviii)(xxviii)R1

R1R1

CHO +






4-





2O4


CHO

+NC

OO

2196 21912

(xxix)

N

CN

OH

21914

N

CN

OH

21915

21913R1

R1

NH2

NH2

(xxix) TiO2NPs MW


O

R X

N

R

X

O O

N

RO

O

21917

21916

21918

2191921920

(xxx) (xxx)NH2

R1

R2

R1

R2

R1 = R2 = H CH3




3H was


3O4nanoparticles






3CN




H N

O

(xxxi)

21913 2196 21921

+

NH2

R2

R2

R2

R1R1




O

O

+OHC

O

OO

NH

O

O

O(xxxii)

21918 21922 2162 21923

21924


OCH2Ph

OCH2Ph

OCH2Ph

OCH2Ph+ +NH4OAC







2-



2








O

O

OH

O

O

NH

O

COOH21925 21926

21927

R1

R1

R2

R2

R2

R2

NH4OAc

R1 = Cl OCH3

R2 = H Me

+ +

CH3

TiO2 NPs


Y

XH

Y

X

HN O

2201 2202 2203

(xxxiii)


NH2

+ RO2C CO2R

CO2R

X = S O NHR = CH3

Y = CH N C2H5


O OMeMeON

R

R

O O

X

+N

N

X(xxxiv)

2211 22122213

2214 2215 2216

(xxxiv)


NH2

+


NHNH2

X = H Et ClR1

R1

= MemiddotOEt


INHR

R

2221 22222223

(xxxv)

(xxxv) 3 PdMIL-101

NH2

+



2231 2232

2233

N

O

N

OH

(xxxvi)


R1

R1

R2

R2

R3

R4

R4

R3

R5

R5


R4 = H Et


R6

R6

R7

R7

+


R OR

OHR

Cl

N

N

O

N O

a

b

c

R

R

N

OEt

R

O

O

Cl

(xxxvii)2234 2235 2236

2237

2238

2239N Cl N Cl

NaBH4 SOCl2


R =










N Cl

CHO

N Cl

OH

22310 22311

(xxxviii)



HN O

OCl RCl

N O

O

Cl

R

Cl

X

22312 2231422313

(xxxix)+

R =

X = CH3 OCH3




3F(H2O)2O(bdc)







3 Conclusions



N

NH

N

Cl

Cl N

N

NCl

O

22315 22316 22317

O

(XL)


+



Acknowledgments


References



















































2nanoparticles































2O4nano par-















2nanoparticles








4rdquo
























2O3)-MCM-41-SO
















3Has a green nano



















2nanopow-























CeramicsJournal of







Biomaterials




Journal of


Journal of





CoatingsJournal of

Advances in








MaterialsJournal of


Nano

materials




O

O N

N

Ph

Ph

(i)

NH2

NH2


+

211 212 213


NCl

N

N

Cl

N

O

222221 223

(ii)

H2NHN

+



N

O

225a

225b

225c224

N

N

226

NR

(iii)

NHNH2

NHNH2 Ac2O

CH3NHNH2



Cl O

HN

O

N

HN

Cl

(iv)

231 232 233

NH2

+




O

O

O

(v)

(vi)

NH

O O

236

N

O OPh

237

234 235


+

C6H5


(vii)

(viii)241

COOH

COOH

N

O

O

N

O

X

242

243



X = O S NH









251

O

252

Br

253O

Br

254

255

O

256

BHO

HO

257

NN

N

R258

Na+NminusminusN

R1

N+

Phenacyl bromide254


azide 251

Styrene oxide256

sodium azide251 and

phenylacetylene255



azide 251



255

123-

triazole



255


OH

O

+ O

OEtO O

261 262 263

(ix)

R1

R1

R2

R3

R3 R4

R2

R4



H OH OMe Et2N








O O OO O

OH R OH

O

OH

(x)

271 272 273

RCHO+


piperonyl


OO HO

(xi)O

HNO

281 282 283284

H2N NH2

++



NC CN (xii)

291 292

O

O

RNC CN

293

O

R

O

NC CNCN

NH2

+



NC CN

294 295

(xiii)(xiv)(xv)

(xvi)

O

OArNC

EtOOC

298

O

CNAr

EtOOC

2911

299

O

O

O

Ar

CN

2910

H3C

NH2

NH2



+

COCH3

H2N

PhndashCHO



N

O

2912

N

O

2913

NC CN

295

(xvii)

CN


+

NH2


NN

CHOMeO OMe

O O

N N

NH

Cl

Me Me

Cl

(xviii)

2101

2102

2103 2104

AcONH4

+

+

MeO2C CO2Me



O

NH

HN O

2111 2112 2113 2114(xix)

H2N NH2

R2

R2

R2

R3

R3

R3

+ +R1

R1

R4

R1 =


R4ndashNC



CHO

OH

O

Ph

NH

O N

O

2121 2122 2123 2124

(xx)


+ +



CHO

O

OO

2131 2133

(xxi)

O

O

2132

NO2

NO2

+



N

OCN

CN

N

N

NHCN

2141 2142 2143 2144

(xxii)Cl Cl

Cl Cl

+ +

NH2

(xxii) 120572-Fe2O

3-MCM-41-SO






4 CuCl

2 Cu (NO









XH(xxiii)

CHON

XR

NH2

+ R1

X = N 2151X = S 2152

R1 = 2153


∘C

X = NH 2154

R1 = Cl NO2 Me OMe

X = S 2155


O

O

Ph

Ph

2161

CHO

2162 2163

(xxiv)

NN

PhPh

2164

+ + NH2








2and TiO

2nanoparticles as







2O3nanopowder








NC CN

NH

N

N

R

CN

CHO

X2171 2172 2173

2174

(xxv)+ + NH2

NH2

R998400

R998400

R998400

= Ph NH2



O

R

N

NOAr

Ar

R

O

2181 2 182 2183 2184

(xxvi)+ + Ar-NH2

R = H CH3












2O3)-MCM-





OH

N

O OBase argon

2191 2192 2193

2195

OH

2194

(xxvii)

R1 R1

R1

+

+

R2R2

R2

R3

R3

R1 = R2 = Ph 234-MeC6H4 4-OMeC6 3C6H4


NH2

H4 4-CF


O

NH

COOH

NC CN N

OCN

NH

O

N

OCN

NH

O

O

NH

COOH

2196 2197

21982199

21910

21911

(xxviii)(xxviii)R1

R1R1

CHO +






4-





2O4


CHO

+NC

OO

2196 21912

(xxix)

N

CN

OH

21914

N

CN

OH

21915

21913R1

R1

NH2

NH2

(xxix) TiO2NPs MW


O

R X

N

R

X

O O

N

RO

O

21917

21916

21918

2191921920

(xxx) (xxx)NH2

R1

R2

R1

R2

R1 = R2 = H CH3




3H was


3O4nanoparticles






3CN




H N

O

(xxxi)

21913 2196 21921

+

NH2

R2

R2

R2

R1R1




O

O

+OHC

O

OO

NH

O

O

O(xxxii)

21918 21922 2162 21923

21924


OCH2Ph

OCH2Ph

OCH2Ph

OCH2Ph+ +NH4OAC







2-



2








O

O

OH

O

O

NH

O

COOH21925 21926

21927

R1

R1

R2

R2

R2

R2

NH4OAc

R1 = Cl OCH3

R2 = H Me

+ +

CH3

TiO2 NPs


Y

XH

Y

X

HN O

2201 2202 2203

(xxxiii)


NH2

+ RO2C CO2R

CO2R

X = S O NHR = CH3

Y = CH N C2H5


O OMeMeON

R

R

O O

X

+N

N

X(xxxiv)

2211 22122213

2214 2215 2216

(xxxiv)


NH2

+


NHNH2

X = H Et ClR1

R1

= MemiddotOEt


INHR

R

2221 22222223

(xxxv)

(xxxv) 3 PdMIL-101

NH2

+



2231 2232

2233

N

O

N

OH

(xxxvi)


R1

R1

R2

R2

R3

R4

R4

R3

R5

R5


R4 = H Et


R6

R6

R7

R7

+


R OR

OHR

Cl

N

N

O

N O

a

b

c

R

R

N

OEt

R

O

O

Cl

(xxxvii)2234 2235 2236

2237

2238

2239N Cl N Cl

NaBH4 SOCl2


R =










N Cl

CHO

N Cl

OH

22310 22311

(xxxviii)



HN O

OCl RCl

N O

O

Cl

R

Cl

X

22312 2231422313

(xxxix)+

R =

X = CH3 OCH3




3F(H2O)2O(bdc)







3 Conclusions



N

NH

N

Cl

Cl N

N

NCl

O

22315 22316 22317

O

(XL)


+



Acknowledgments


References



















































2nanoparticles































2O4nano par-















2nanoparticles








4rdquo
























2O3)-MCM-41-SO
















3Has a green nano



















2nanopow-























CeramicsJournal of







Biomaterials




Journal of


Journal of





CoatingsJournal of

Advances in








MaterialsJournal of


Nano

materials




O

O

O

(v)

(vi)

NH

O O

236

N

O OPh

237

234 235


+

C6H5


(vii)

(viii)241

COOH

COOH

N

O

O

N

O

X

242

243



X = O S NH









251

O

252

Br

253O

Br

254

255

O

256

BHO

HO

257

NN

N

R258

Na+NminusminusN

R1

N+

Phenacyl bromide254


azide 251

Styrene oxide256

sodium azide251 and

phenylacetylene255



azide 251



255

123-

triazole



255


OH

O

+ O

OEtO O

261 262 263

(ix)

R1

R1

R2

R3

R3 R4

R2

R4



H OH OMe Et2N








O O OO O

OH R OH

O

OH

(x)

271 272 273

RCHO+


piperonyl


OO HO

(xi)O

HNO

281 282 283284

H2N NH2

++



NC CN (xii)

291 292

O

O

RNC CN

293

O

R

O

NC CNCN

NH2

+



NC CN

294 295

(xiii)(xiv)(xv)

(xvi)

O

OArNC

EtOOC

298

O

CNAr

EtOOC

2911

299

O

O

O

Ar

CN

2910

H3C

NH2

NH2



+

COCH3

H2N

PhndashCHO



N

O

2912

N

O

2913

NC CN

295

(xvii)

CN


+

NH2


NN

CHOMeO OMe

O O

N N

NH

Cl

Me Me

Cl

(xviii)

2101

2102

2103 2104

AcONH4

+

+

MeO2C CO2Me



O

NH

HN O

2111 2112 2113 2114(xix)

H2N NH2

R2

R2

R2

R3

R3

R3

+ +R1

R1

R4

R1 =


R4ndashNC



CHO

OH

O

Ph

NH

O N

O

2121 2122 2123 2124

(xx)


+ +



CHO

O

OO

2131 2133

(xxi)

O

O

2132

NO2

NO2

+



N

OCN

CN

N

N

NHCN

2141 2142 2143 2144

(xxii)Cl Cl

Cl Cl

+ +

NH2

(xxii) 120572-Fe2O

3-MCM-41-SO






4 CuCl

2 Cu (NO









XH(xxiii)

CHON

XR

NH2

+ R1

X = N 2151X = S 2152

R1 = 2153


∘C

X = NH 2154

R1 = Cl NO2 Me OMe

X = S 2155


O

O

Ph

Ph

2161

CHO

2162 2163

(xxiv)

NN

PhPh

2164

+ + NH2








2and TiO

2nanoparticles as







2O3nanopowder








NC CN

NH

N

N

R

CN

CHO

X2171 2172 2173

2174

(xxv)+ + NH2

NH2

R998400

R998400

R998400

= Ph NH2



O

R

N

NOAr

Ar

R

O

2181 2 182 2183 2184

(xxvi)+ + Ar-NH2

R = H CH3












2O3)-MCM-





OH

N

O OBase argon

2191 2192 2193

2195

OH

2194

(xxvii)

R1 R1

R1

+

+

R2R2

R2

R3

R3

R1 = R2 = Ph 234-MeC6H4 4-OMeC6 3C6H4


NH2

H4 4-CF


O

NH

COOH

NC CN N

OCN

NH

O

N

OCN

NH

O

O

NH

COOH

2196 2197

21982199

21910

21911

(xxviii)(xxviii)R1

R1R1

CHO +






4-





2O4


CHO

+NC

OO

2196 21912

(xxix)

N

CN

OH

21914

N

CN

OH

21915

21913R1

R1

NH2

NH2

(xxix) TiO2NPs MW


O

R X

N

R

X

O O

N

RO

O

21917

21916

21918

2191921920

(xxx) (xxx)NH2

R1

R2

R1

R2

R1 = R2 = H CH3




3H was


3O4nanoparticles






3CN




H N

O

(xxxi)

21913 2196 21921

+

NH2

R2

R2

R2

R1R1




O

O

+OHC

O

OO

NH

O

O

O(xxxii)

21918 21922 2162 21923

21924


OCH2Ph

OCH2Ph

OCH2Ph

OCH2Ph+ +NH4OAC







2-



2








O

O

OH

O

O

NH

O

COOH21925 21926

21927

R1

R1

R2

R2

R2

R2

NH4OAc

R1 = Cl OCH3

R2 = H Me

+ +

CH3

TiO2 NPs


Y

XH

Y

X

HN O

2201 2202 2203

(xxxiii)


NH2

+ RO2C CO2R

CO2R

X = S O NHR = CH3

Y = CH N C2H5


O OMeMeON

R

R

O O

X

+N

N

X(xxxiv)

2211 22122213

2214 2215 2216

(xxxiv)


NH2

+


NHNH2

X = H Et ClR1

R1

= MemiddotOEt


INHR

R

2221 22222223

(xxxv)

(xxxv) 3 PdMIL-101

NH2

+



2231 2232

2233

N

O

N

OH

(xxxvi)


R1

R1

R2

R2

R3

R4

R4

R3

R5

R5


R4 = H Et


R6

R6

R7

R7

+


R OR

OHR

Cl

N

N

O

N O

a

b

c

R

R

N

OEt

R

O

O

Cl

(xxxvii)2234 2235 2236

2237

2238

2239N Cl N Cl

NaBH4 SOCl2


R =










N Cl

CHO

N Cl

OH

22310 22311

(xxxviii)



HN O

OCl RCl

N O

O

Cl

R

Cl

X

22312 2231422313

(xxxix)+

R =

X = CH3 OCH3




3F(H2O)2O(bdc)







3 Conclusions



N

NH

N

Cl

Cl N

N

NCl

O

22315 22316 22317

O

(XL)


+



Acknowledgments


References



















































2nanoparticles































2O4nano par-















2nanoparticles








4rdquo
























2O3)-MCM-41-SO
















3Has a green nano



















2nanopow-























CeramicsJournal of







Biomaterials




Journal of


Journal of





CoatingsJournal of

Advances in








MaterialsJournal of


Nano

materials




251

O

252

Br

253O

Br

254

255

O

256

BHO

HO

257

NN

N

R258

Na+NminusminusN

R1

N+

Phenacyl bromide254


azide 251

Styrene oxide256

sodium azide251 and

phenylacetylene255



azide 251



255

123-

triazole



255


OH

O

+ O

OEtO O

261 262 263

(ix)

R1

R1

R2

R3

R3 R4

R2

R4



H OH OMe Et2N








O O OO O

OH R OH

O

OH

(x)

271 272 273

RCHO+


piperonyl


OO HO

(xi)O

HNO

281 282 283284

H2N NH2

++



NC CN (xii)

291 292

O

O

RNC CN

293

O

R

O

NC CNCN

NH2

+



NC CN

294 295

(xiii)(xiv)(xv)

(xvi)

O

OArNC

EtOOC

298

O

CNAr

EtOOC

2911

299

O

O

O

Ar

CN

2910

H3C

NH2

NH2



+

COCH3

H2N

PhndashCHO



N

O

2912

N

O

2913

NC CN

295

(xvii)

CN


+

NH2


NN

CHOMeO OMe

O O

N N

NH

Cl

Me Me

Cl

(xviii)

2101

2102

2103 2104

AcONH4

+

+

MeO2C CO2Me



O

NH

HN O

2111 2112 2113 2114(xix)

H2N NH2

R2

R2

R2

R3

R3

R3

+ +R1

R1

R4

R1 =


R4ndashNC



CHO

OH

O

Ph

NH

O N

O

2121 2122 2123 2124

(xx)


+ +



CHO

O

OO

2131 2133

(xxi)

O

O

2132

NO2

NO2

+



N

OCN

CN

N

N

NHCN

2141 2142 2143 2144

(xxii)Cl Cl

Cl Cl

+ +

NH2

(xxii) 120572-Fe2O

3-MCM-41-SO






4 CuCl

2 Cu (NO









XH(xxiii)

CHON

XR

NH2

+ R1

X = N 2151X = S 2152

R1 = 2153


∘C

X = NH 2154

R1 = Cl NO2 Me OMe

X = S 2155


O

O

Ph

Ph

2161

CHO

2162 2163

(xxiv)

NN

PhPh

2164

+ + NH2








2and TiO

2nanoparticles as







2O3nanopowder








NC CN

NH

N

N

R

CN

CHO

X2171 2172 2173

2174

(xxv)+ + NH2

NH2

R998400

R998400

R998400

= Ph NH2



O

R

N

NOAr

Ar

R

O

2181 2 182 2183 2184

(xxvi)+ + Ar-NH2

R = H CH3












2O3)-MCM-





OH

N

O OBase argon

2191 2192 2193

2195

OH

2194

(xxvii)

R1 R1

R1

+

+

R2R2

R2

R3

R3

R1 = R2 = Ph 234-MeC6H4 4-OMeC6 3C6H4


NH2

H4 4-CF


O

NH

COOH

NC CN N

OCN

NH

O

N

OCN

NH

O

O

NH

COOH

2196 2197

21982199

21910

21911

(xxviii)(xxviii)R1

R1R1

CHO +






4-





2O4


CHO

+NC

OO

2196 21912

(xxix)

N

CN

OH

21914

N

CN

OH

21915

21913R1

R1

NH2

NH2

(xxix) TiO2NPs MW


O

R X

N

R

X

O O

N

RO

O

21917

21916

21918

2191921920

(xxx) (xxx)NH2

R1

R2

R1

R2

R1 = R2 = H CH3




3H was


3O4nanoparticles






3CN




H N

O

(xxxi)

21913 2196 21921

+

NH2

R2

R2

R2

R1R1




O

O

+OHC

O

OO

NH

O

O

O(xxxii)

21918 21922 2162 21923

21924


OCH2Ph

OCH2Ph

OCH2Ph

OCH2Ph+ +NH4OAC







2-



2








O

O

OH

O

O

NH

O

COOH21925 21926

21927

R1

R1

R2

R2

R2

R2

NH4OAc

R1 = Cl OCH3

R2 = H Me

+ +

CH3

TiO2 NPs


Y

XH

Y

X

HN O

2201 2202 2203

(xxxiii)


NH2

+ RO2C CO2R

CO2R

X = S O NHR = CH3

Y = CH N C2H5


O OMeMeON

R

R

O O

X

+N

N

X(xxxiv)

2211 22122213

2214 2215 2216

(xxxiv)


NH2

+


NHNH2

X = H Et ClR1

R1

= MemiddotOEt


INHR

R

2221 22222223

(xxxv)

(xxxv) 3 PdMIL-101

NH2

+



2231 2232

2233

N

O

N

OH

(xxxvi)


R1

R1

R2

R2

R3

R4

R4

R3

R5

R5


R4 = H Et


R6

R6

R7

R7

+


R OR

OHR

Cl

N

N

O

N O

a

b

c

R

R

N

OEt

R

O

O

Cl

(xxxvii)2234 2235 2236

2237

2238

2239N Cl N Cl

NaBH4 SOCl2


R =










N Cl

CHO

N Cl

OH

22310 22311

(xxxviii)



HN O

OCl RCl

N O

O

Cl

R

Cl

X

22312 2231422313

(xxxix)+

R =

X = CH3 OCH3




3F(H2O)2O(bdc)







3 Conclusions



N

NH

N

Cl

Cl N

N

NCl

O

22315 22316 22317

O

(XL)


+



Acknowledgments


References



















































2nanoparticles































2O4nano par-















2nanoparticles








4rdquo
























2O3)-MCM-41-SO
















3Has a green nano



















2nanopow-























CeramicsJournal of







Biomaterials




Journal of


Journal of





CoatingsJournal of

Advances in








MaterialsJournal of


Nano

materials




O O OO O

OH R OH

O

OH

(x)

271 272 273

RCHO+


piperonyl


OO HO

(xi)O

HNO

281 282 283284

H2N NH2

++



NC CN (xii)

291 292

O

O

RNC CN

293

O

R

O

NC CNCN

NH2

+



NC CN

294 295

(xiii)(xiv)(xv)

(xvi)

O

OArNC

EtOOC

298

O

CNAr

EtOOC

2911

299

O

O

O

Ar

CN

2910

H3C

NH2

NH2



+

COCH3

H2N

PhndashCHO



N

O

2912

N

O

2913

NC CN

295

(xvii)

CN


+

NH2


NN

CHOMeO OMe

O O

N N

NH

Cl

Me Me

Cl

(xviii)

2101

2102

2103 2104

AcONH4

+

+

MeO2C CO2Me



O

NH

HN O

2111 2112 2113 2114(xix)

H2N NH2

R2

R2

R2

R3

R3

R3

+ +R1

R1

R4

R1 =


R4ndashNC



CHO

OH

O

Ph

NH

O N

O

2121 2122 2123 2124

(xx)


+ +



CHO

O

OO

2131 2133

(xxi)

O

O

2132

NO2

NO2

+



N

OCN

CN

N

N

NHCN

2141 2142 2143 2144

(xxii)Cl Cl

Cl Cl

+ +

NH2

(xxii) 120572-Fe2O

3-MCM-41-SO






4 CuCl

2 Cu (NO









XH(xxiii)

CHON

XR

NH2

+ R1

X = N 2151X = S 2152

R1 = 2153


∘C

X = NH 2154

R1 = Cl NO2 Me OMe

X = S 2155


O

O

Ph

Ph

2161

CHO

2162 2163

(xxiv)

NN

PhPh

2164

+ + NH2








2and TiO

2nanoparticles as







2O3nanopowder








NC CN

NH

N

N

R

CN

CHO

X2171 2172 2173

2174

(xxv)+ + NH2

NH2

R998400

R998400

R998400

= Ph NH2



O

R

N

NOAr

Ar

R

O

2181 2 182 2183 2184

(xxvi)+ + Ar-NH2

R = H CH3












2O3)-MCM-





OH

N

O OBase argon

2191 2192 2193

2195

OH

2194

(xxvii)

R1 R1

R1

+

+

R2R2

R2

R3

R3

R1 = R2 = Ph 234-MeC6H4 4-OMeC6 3C6H4


NH2

H4 4-CF


O

NH

COOH

NC CN N

OCN

NH

O

N

OCN

NH

O

O

NH

COOH

2196 2197

21982199

21910

21911

(xxviii)(xxviii)R1

R1R1

CHO +






4-





2O4


CHO

+NC

OO

2196 21912

(xxix)

N

CN

OH

21914

N

CN

OH

21915

21913R1

R1

NH2

NH2

(xxix) TiO2NPs MW


O

R X

N

R

X

O O

N

RO

O

21917

21916

21918

2191921920

(xxx) (xxx)NH2

R1

R2

R1

R2

R1 = R2 = H CH3




3H was


3O4nanoparticles






3CN




H N

O

(xxxi)

21913 2196 21921

+

NH2

R2

R2

R2

R1R1




O

O

+OHC

O

OO

NH

O

O

O(xxxii)

21918 21922 2162 21923

21924


OCH2Ph

OCH2Ph

OCH2Ph

OCH2Ph+ +NH4OAC







2-



2








O

O

OH

O

O

NH

O

COOH21925 21926

21927

R1

R1

R2

R2

R2

R2

NH4OAc

R1 = Cl OCH3

R2 = H Me

+ +

CH3

TiO2 NPs


Y

XH

Y

X

HN O

2201 2202 2203

(xxxiii)


NH2

+ RO2C CO2R

CO2R

X = S O NHR = CH3

Y = CH N C2H5


O OMeMeON

R

R

O O

X

+N

N

X(xxxiv)

2211 22122213

2214 2215 2216

(xxxiv)


NH2

+


NHNH2

X = H Et ClR1

R1

= MemiddotOEt


INHR

R

2221 22222223

(xxxv)

(xxxv) 3 PdMIL-101

NH2

+



2231 2232

2233

N

O

N

OH

(xxxvi)


R1

R1

R2

R2

R3

R4

R4

R3

R5

R5


R4 = H Et


R6

R6

R7

R7

+


R OR

OHR

Cl

N

N

O

N O

a

b

c

R

R

N

OEt

R

O

O

Cl

(xxxvii)2234 2235 2236

2237

2238

2239N Cl N Cl

NaBH4 SOCl2


R =










N Cl

CHO

N Cl

OH

22310 22311

(xxxviii)



HN O

OCl RCl

N O

O

Cl

R

Cl

X

22312 2231422313

(xxxix)+

R =

X = CH3 OCH3




3F(H2O)2O(bdc)







3 Conclusions



N

NH

N

Cl

Cl N

N

NCl

O

22315 22316 22317

O

(XL)


+



Acknowledgments


References



















































2nanoparticles































2O4nano par-















2nanoparticles








4rdquo
























2O3)-MCM-41-SO
















3Has a green nano



















2nanopow-























CeramicsJournal of







Biomaterials




Journal of


Journal of





CoatingsJournal of

Advances in








MaterialsJournal of


Nano

materials




N

O

2912

N

O

2913

NC CN

295

(xvii)

CN


+

NH2


NN

CHOMeO OMe

O O

N N

NH

Cl

Me Me

Cl

(xviii)

2101

2102

2103 2104

AcONH4

+

+

MeO2C CO2Me



O

NH

HN O

2111 2112 2113 2114(xix)

H2N NH2

R2

R2

R2

R3

R3

R3

+ +R1

R1

R4

R1 =


R4ndashNC



CHO

OH

O

Ph

NH

O N

O

2121 2122 2123 2124

(xx)


+ +



CHO

O

OO

2131 2133

(xxi)

O

O

2132

NO2

NO2

+



N

OCN

CN

N

N

NHCN

2141 2142 2143 2144

(xxii)Cl Cl

Cl Cl

+ +

NH2

(xxii) 120572-Fe2O

3-MCM-41-SO






4 CuCl

2 Cu (NO









XH(xxiii)

CHON

XR

NH2

+ R1

X = N 2151X = S 2152

R1 = 2153


∘C

X = NH 2154

R1 = Cl NO2 Me OMe

X = S 2155


O

O

Ph

Ph

2161

CHO

2162 2163

(xxiv)

NN

PhPh

2164

+ + NH2








2and TiO

2nanoparticles as







2O3nanopowder








NC CN

NH

N

N

R

CN

CHO

X2171 2172 2173

2174

(xxv)+ + NH2

NH2

R998400

R998400

R998400

= Ph NH2



O

R

N

NOAr

Ar

R

O

2181 2 182 2183 2184

(xxvi)+ + Ar-NH2

R = H CH3












2O3)-MCM-





OH

N

O OBase argon

2191 2192 2193

2195

OH

2194

(xxvii)

R1 R1

R1

+

+

R2R2

R2

R3

R3

R1 = R2 = Ph 234-MeC6H4 4-OMeC6 3C6H4


NH2

H4 4-CF


O

NH

COOH

NC CN N

OCN

NH

O

N

OCN

NH

O

O

NH

COOH

2196 2197

21982199

21910

21911

(xxviii)(xxviii)R1

R1R1

CHO +






4-





2O4


CHO

+NC

OO

2196 21912

(xxix)

N

CN

OH

21914

N

CN

OH

21915

21913R1

R1

NH2

NH2

(xxix) TiO2NPs MW


O

R X

N

R

X

O O

N

RO

O

21917

21916

21918

2191921920

(xxx) (xxx)NH2

R1

R2

R1

R2

R1 = R2 = H CH3




3H was


3O4nanoparticles






3CN




H N

O

(xxxi)

21913 2196 21921

+

NH2

R2

R2

R2

R1R1




O

O

+OHC

O

OO

NH

O

O

O(xxxii)

21918 21922 2162 21923

21924


OCH2Ph

OCH2Ph

OCH2Ph

OCH2Ph+ +NH4OAC







2-



2








O

O

OH

O

O

NH

O

COOH21925 21926

21927

R1

R1

R2

R2

R2

R2

NH4OAc

R1 = Cl OCH3

R2 = H Me

+ +

CH3

TiO2 NPs


Y

XH

Y

X

HN O

2201 2202 2203

(xxxiii)


NH2

+ RO2C CO2R

CO2R

X = S O NHR = CH3

Y = CH N C2H5


O OMeMeON

R

R

O O

X

+N

N

X(xxxiv)

2211 22122213

2214 2215 2216

(xxxiv)


NH2

+


NHNH2

X = H Et ClR1

R1

= MemiddotOEt


INHR

R

2221 22222223

(xxxv)

(xxxv) 3 PdMIL-101

NH2

+



2231 2232

2233

N

O

N

OH

(xxxvi)


R1

R1

R2

R2

R3

R4

R4

R3

R5

R5


R4 = H Et


R6

R6

R7

R7

+


R OR

OHR

Cl

N

N

O

N O

a

b

c

R

R

N

OEt

R

O

O

Cl

(xxxvii)2234 2235 2236

2237

2238

2239N Cl N Cl

NaBH4 SOCl2


R =










N Cl

CHO

N Cl

OH

22310 22311

(xxxviii)



HN O

OCl RCl

N O

O

Cl

R

Cl

X

22312 2231422313

(xxxix)+

R =

X = CH3 OCH3




3F(H2O)2O(bdc)







3 Conclusions



N

NH

N

Cl

Cl N

N

NCl

O

22315 22316 22317

O

(XL)


+



Acknowledgments


References



















































2nanoparticles































2O4nano par-















2nanoparticles








4rdquo
























2O3)-MCM-41-SO
















3Has a green nano



















2nanopow-























CeramicsJournal of







Biomaterials




Journal of


Journal of





CoatingsJournal of

Advances in








MaterialsJournal of


Nano

materials




CHO

O

OO

2131 2133

(xxi)

O

O

2132

NO2

NO2

+



N

OCN

CN

N

N

NHCN

2141 2142 2143 2144

(xxii)Cl Cl

Cl Cl

+ +

NH2

(xxii) 120572-Fe2O

3-MCM-41-SO






4 CuCl

2 Cu (NO









XH(xxiii)

CHON

XR

NH2

+ R1

X = N 2151X = S 2152

R1 = 2153


∘C

X = NH 2154

R1 = Cl NO2 Me OMe

X = S 2155


O

O

Ph

Ph

2161

CHO

2162 2163

(xxiv)

NN

PhPh

2164

+ + NH2








2and TiO

2nanoparticles as







2O3nanopowder








NC CN

NH

N

N

R

CN

CHO

X2171 2172 2173

2174

(xxv)+ + NH2

NH2

R998400

R998400

R998400

= Ph NH2



O

R

N

NOAr

Ar

R

O

2181 2 182 2183 2184

(xxvi)+ + Ar-NH2

R = H CH3












2O3)-MCM-





OH

N

O OBase argon

2191 2192 2193

2195

OH

2194

(xxvii)

R1 R1

R1

+

+

R2R2

R2

R3

R3

R1 = R2 = Ph 234-MeC6H4 4-OMeC6 3C6H4


NH2

H4 4-CF


O

NH

COOH

NC CN N

OCN

NH

O

N

OCN

NH

O

O

NH

COOH

2196 2197

21982199

21910

21911

(xxviii)(xxviii)R1

R1R1

CHO +






4-





2O4


CHO

+NC

OO

2196 21912

(xxix)

N

CN

OH

21914

N

CN

OH

21915

21913R1

R1

NH2

NH2

(xxix) TiO2NPs MW


O

R X

N

R

X

O O

N

RO

O

21917

21916

21918

2191921920

(xxx) (xxx)NH2

R1

R2

R1

R2

R1 = R2 = H CH3




3H was


3O4nanoparticles






3CN




H N

O

(xxxi)

21913 2196 21921

+

NH2

R2

R2

R2

R1R1




O

O

+OHC

O

OO

NH

O

O

O(xxxii)

21918 21922 2162 21923

21924


OCH2Ph

OCH2Ph

OCH2Ph

OCH2Ph+ +NH4OAC







2-



2








O

O

OH

O

O

NH

O

COOH21925 21926

21927

R1

R1

R2

R2

R2

R2

NH4OAc

R1 = Cl OCH3

R2 = H Me

+ +

CH3

TiO2 NPs


Y

XH

Y

X

HN O

2201 2202 2203

(xxxiii)


NH2

+ RO2C CO2R

CO2R

X = S O NHR = CH3

Y = CH N C2H5


O OMeMeON

R

R

O O

X

+N

N

X(xxxiv)

2211 22122213

2214 2215 2216

(xxxiv)


NH2

+


NHNH2

X = H Et ClR1

R1

= MemiddotOEt


INHR

R

2221 22222223

(xxxv)

(xxxv) 3 PdMIL-101

NH2

+



2231 2232

2233

N

O

N

OH

(xxxvi)


R1

R1

R2

R2

R3

R4

R4

R3

R5

R5


R4 = H Et


R6

R6

R7

R7

+


R OR

OHR

Cl

N

N

O

N O

a

b

c

R

R

N

OEt

R

O

O

Cl

(xxxvii)2234 2235 2236

2237

2238

2239N Cl N Cl

NaBH4 SOCl2


R =










N Cl

CHO

N Cl

OH

22310 22311

(xxxviii)



HN O

OCl RCl

N O

O

Cl

R

Cl

X

22312 2231422313

(xxxix)+

R =

X = CH3 OCH3




3F(H2O)2O(bdc)







3 Conclusions



N

NH

N

Cl

Cl N

N

NCl

O

22315 22316 22317

O

(XL)


+



Acknowledgments


References



















































2nanoparticles































2O4nano par-















2nanoparticles








4rdquo
























2O3)-MCM-41-SO
















3Has a green nano



















2nanopow-























CeramicsJournal of







Biomaterials




Journal of


Journal of





CoatingsJournal of

Advances in








MaterialsJournal of


Nano

materials




XH(xxiii)

CHON

XR

NH2

+ R1

X = N 2151X = S 2152

R1 = 2153


∘C

X = NH 2154

R1 = Cl NO2 Me OMe

X = S 2155


O

O

Ph

Ph

2161

CHO

2162 2163

(xxiv)

NN

PhPh

2164

+ + NH2








2and TiO

2nanoparticles as







2O3nanopowder








NC CN

NH

N

N

R

CN

CHO

X2171 2172 2173

2174

(xxv)+ + NH2

NH2

R998400

R998400

R998400

= Ph NH2



O

R

N

NOAr

Ar

R

O

2181 2 182 2183 2184

(xxvi)+ + Ar-NH2

R = H CH3












2O3)-MCM-





OH

N

O OBase argon

2191 2192 2193

2195

OH

2194

(xxvii)

R1 R1

R1

+

+

R2R2

R2

R3

R3

R1 = R2 = Ph 234-MeC6H4 4-OMeC6 3C6H4


NH2

H4 4-CF


O

NH

COOH

NC CN N

OCN

NH

O

N

OCN

NH

O

O

NH

COOH

2196 2197

21982199

21910

21911

(xxviii)(xxviii)R1

R1R1

CHO +






4-





2O4


CHO

+NC

OO

2196 21912

(xxix)

N

CN

OH

21914

N

CN

OH

21915

21913R1

R1

NH2

NH2

(xxix) TiO2NPs MW


O

R X

N

R

X

O O

N

RO

O

21917

21916

21918

2191921920

(xxx) (xxx)NH2

R1

R2

R1

R2

R1 = R2 = H CH3




3H was


3O4nanoparticles






3CN




H N

O

(xxxi)

21913 2196 21921

+

NH2

R2

R2

R2

R1R1




O

O

+OHC

O

OO

NH

O

O

O(xxxii)

21918 21922 2162 21923

21924


OCH2Ph

OCH2Ph

OCH2Ph

OCH2Ph+ +NH4OAC







2-



2








O

O

OH

O

O

NH

O

COOH21925 21926

21927

R1

R1

R2

R2

R2

R2

NH4OAc

R1 = Cl OCH3

R2 = H Me

+ +

CH3

TiO2 NPs


Y

XH

Y

X

HN O

2201 2202 2203

(xxxiii)


NH2

+ RO2C CO2R

CO2R

X = S O NHR = CH3

Y = CH N C2H5


O OMeMeON

R

R

O O

X

+N

N

X(xxxiv)

2211 22122213

2214 2215 2216

(xxxiv)


NH2

+


NHNH2

X = H Et ClR1

R1

= MemiddotOEt


INHR

R

2221 22222223

(xxxv)

(xxxv) 3 PdMIL-101

NH2

+



2231 2232

2233

N

O

N

OH

(xxxvi)


R1

R1

R2

R2

R3

R4

R4

R3

R5

R5


R4 = H Et


R6

R6

R7

R7

+


R OR

OHR

Cl

N

N

O

N O

a

b

c

R

R

N

OEt

R

O

O

Cl

(xxxvii)2234 2235 2236

2237

2238

2239N Cl N Cl

NaBH4 SOCl2


R =










N Cl

CHO

N Cl

OH

22310 22311

(xxxviii)



HN O

OCl RCl

N O

O

Cl

R

Cl

X

22312 2231422313

(xxxix)+

R =

X = CH3 OCH3




3F(H2O)2O(bdc)







3 Conclusions



N

NH

N

Cl

Cl N

N

NCl

O

22315 22316 22317

O

(XL)


+



Acknowledgments


References



















































2nanoparticles































2O4nano par-















2nanoparticles








4rdquo
























2O3)-MCM-41-SO
















3Has a green nano



















2nanopow-























CeramicsJournal of







Biomaterials




Journal of


Journal of





CoatingsJournal of

Advances in








MaterialsJournal of


Nano

materials




NC CN

NH

N

N

R

CN

CHO

X2171 2172 2173

2174

(xxv)+ + NH2

NH2

R998400

R998400

R998400

= Ph NH2



O

R

N

NOAr

Ar

R

O

2181 2 182 2183 2184

(xxvi)+ + Ar-NH2

R = H CH3












2O3)-MCM-





OH

N

O OBase argon

2191 2192 2193

2195

OH

2194

(xxvii)

R1 R1

R1

+

+

R2R2

R2

R3

R3

R1 = R2 = Ph 234-MeC6H4 4-OMeC6 3C6H4


NH2

H4 4-CF


O

NH

COOH

NC CN N

OCN

NH

O

N

OCN

NH

O

O

NH

COOH

2196 2197

21982199

21910

21911

(xxviii)(xxviii)R1

R1R1

CHO +






4-





2O4


CHO

+NC

OO

2196 21912

(xxix)

N

CN

OH

21914

N

CN

OH

21915

21913R1

R1

NH2

NH2

(xxix) TiO2NPs MW


O

R X

N

R

X

O O

N

RO

O

21917

21916

21918

2191921920

(xxx) (xxx)NH2

R1

R2

R1

R2

R1 = R2 = H CH3




3H was


3O4nanoparticles






3CN




H N

O

(xxxi)

21913 2196 21921

+

NH2

R2

R2

R2

R1R1




O

O

+OHC

O

OO

NH

O

O

O(xxxii)

21918 21922 2162 21923

21924


OCH2Ph

OCH2Ph

OCH2Ph

OCH2Ph+ +NH4OAC







2-



2








O

O

OH

O

O

NH

O

COOH21925 21926

21927

R1

R1

R2

R2

R2

R2

NH4OAc

R1 = Cl OCH3

R2 = H Me

+ +

CH3

TiO2 NPs


Y

XH

Y

X

HN O

2201 2202 2203

(xxxiii)


NH2

+ RO2C CO2R

CO2R

X = S O NHR = CH3

Y = CH N C2H5


O OMeMeON

R

R

O O

X

+N

N

X(xxxiv)

2211 22122213

2214 2215 2216

(xxxiv)


NH2

+


NHNH2

X = H Et ClR1

R1

= MemiddotOEt


INHR

R

2221 22222223

(xxxv)

(xxxv) 3 PdMIL-101

NH2

+



2231 2232

2233

N

O

N

OH

(xxxvi)


R1

R1

R2

R2

R3

R4

R4

R3

R5

R5


R4 = H Et


R6

R6

R7

R7

+


R OR

OHR

Cl

N

N

O

N O

a

b

c

R

R

N

OEt

R

O

O

Cl

(xxxvii)2234 2235 2236

2237

2238

2239N Cl N Cl

NaBH4 SOCl2


R =










N Cl

CHO

N Cl

OH

22310 22311

(xxxviii)



HN O

OCl RCl

N O

O

Cl

R

Cl

X

22312 2231422313

(xxxix)+

R =

X = CH3 OCH3




3F(H2O)2O(bdc)







3 Conclusions



N

NH

N

Cl

Cl N

N

NCl

O

22315 22316 22317

O

(XL)


+



Acknowledgments


References



















































2nanoparticles































2O4nano par-















2nanoparticles








4rdquo
























2O3)-MCM-41-SO
















3Has a green nano



















2nanopow-























CeramicsJournal of







Biomaterials




Journal of


Journal of





CoatingsJournal of

Advances in








MaterialsJournal of


Nano

materials




OH

N

O OBase argon

2191 2192 2193

2195

OH

2194

(xxvii)

R1 R1

R1

+

+

R2R2

R2

R3

R3

R1 = R2 = Ph 234-MeC6H4 4-OMeC6 3C6H4


NH2

H4 4-CF


O

NH

COOH

NC CN N

OCN

NH

O

N

OCN

NH

O

O

NH

COOH

2196 2197

21982199

21910

21911

(xxviii)(xxviii)R1

R1R1

CHO +






4-





2O4


CHO

+NC

OO

2196 21912

(xxix)

N

CN

OH

21914

N

CN

OH

21915

21913R1

R1

NH2

NH2

(xxix) TiO2NPs MW


O

R X

N

R

X

O O

N

RO

O

21917

21916

21918

2191921920

(xxx) (xxx)NH2

R1

R2

R1

R2

R1 = R2 = H CH3




3H was


3O4nanoparticles






3CN




H N

O

(xxxi)

21913 2196 21921

+

NH2

R2

R2

R2

R1R1




O

O

+OHC

O

OO

NH

O

O

O(xxxii)

21918 21922 2162 21923

21924


OCH2Ph

OCH2Ph

OCH2Ph

OCH2Ph+ +NH4OAC







2-



2








O

O

OH

O

O

NH

O

COOH21925 21926

21927

R1

R1

R2

R2

R2

R2

NH4OAc

R1 = Cl OCH3

R2 = H Me

+ +

CH3

TiO2 NPs


Y

XH

Y

X

HN O

2201 2202 2203

(xxxiii)


NH2

+ RO2C CO2R

CO2R

X = S O NHR = CH3

Y = CH N C2H5


O OMeMeON

R

R

O O

X

+N

N

X(xxxiv)

2211 22122213

2214 2215 2216

(xxxiv)


NH2

+


NHNH2

X = H Et ClR1

R1

= MemiddotOEt


INHR

R

2221 22222223

(xxxv)

(xxxv) 3 PdMIL-101

NH2

+



2231 2232

2233

N

O

N

OH

(xxxvi)


R1

R1

R2

R2

R3

R4

R4

R3

R5

R5


R4 = H Et


R6

R6

R7

R7

+


R OR

OHR

Cl

N

N

O

N O

a

b

c

R

R

N

OEt

R

O

O

Cl

(xxxvii)2234 2235 2236

2237

2238

2239N Cl N Cl

NaBH4 SOCl2


R =










N Cl

CHO

N Cl

OH

22310 22311

(xxxviii)



HN O

OCl RCl

N O

O

Cl

R

Cl

X

22312 2231422313

(xxxix)+

R =

X = CH3 OCH3




3F(H2O)2O(bdc)







3 Conclusions



N

NH

N

Cl

Cl N

N

NCl

O

22315 22316 22317

O

(XL)


+



Acknowledgments


References



















































2nanoparticles































2O4nano par-















2nanoparticles








4rdquo
























2O3)-MCM-41-SO
















3Has a green nano



















2nanopow-























CeramicsJournal of







Biomaterials




Journal of


Journal of





CoatingsJournal of

Advances in








MaterialsJournal of


Nano

materials




CHO

+NC

OO

2196 21912

(xxix)

N

CN

OH

21914

N

CN

OH

21915

21913R1

R1

NH2

NH2

(xxix) TiO2NPs MW


O

R X

N

R

X

O O

N

RO

O

21917

21916

21918

2191921920

(xxx) (xxx)NH2

R1

R2

R1

R2

R1 = R2 = H CH3




3H was


3O4nanoparticles






3CN




H N

O

(xxxi)

21913 2196 21921

+

NH2

R2

R2

R2

R1R1




O

O

+OHC

O

OO

NH

O

O

O(xxxii)

21918 21922 2162 21923

21924


OCH2Ph

OCH2Ph

OCH2Ph

OCH2Ph+ +NH4OAC







2-



2








O

O

OH

O

O

NH

O

COOH21925 21926

21927

R1

R1

R2

R2

R2

R2

NH4OAc

R1 = Cl OCH3

R2 = H Me

+ +

CH3

TiO2 NPs


Y

XH

Y

X

HN O

2201 2202 2203

(xxxiii)


NH2

+ RO2C CO2R

CO2R

X = S O NHR = CH3

Y = CH N C2H5


O OMeMeON

R

R

O O

X

+N

N

X(xxxiv)

2211 22122213

2214 2215 2216

(xxxiv)


NH2

+


NHNH2

X = H Et ClR1

R1

= MemiddotOEt


INHR

R

2221 22222223

(xxxv)

(xxxv) 3 PdMIL-101

NH2

+



2231 2232

2233

N

O

N

OH

(xxxvi)


R1

R1

R2

R2

R3

R4

R4

R3

R5

R5


R4 = H Et


R6

R6

R7

R7

+


R OR

OHR

Cl

N

N

O

N O

a

b

c

R

R

N

OEt

R

O

O

Cl

(xxxvii)2234 2235 2236

2237

2238

2239N Cl N Cl

NaBH4 SOCl2


R =










N Cl

CHO

N Cl

OH

22310 22311

(xxxviii)



HN O

OCl RCl

N O

O

Cl

R

Cl

X

22312 2231422313

(xxxix)+

R =

X = CH3 OCH3




3F(H2O)2O(bdc)







3 Conclusions



N

NH

N

Cl

Cl N

N

NCl

O

22315 22316 22317

O

(XL)


+



Acknowledgments


References



















































2nanoparticles































2O4nano par-















2nanoparticles








4rdquo
























2O3)-MCM-41-SO
















3Has a green nano



















2nanopow-























CeramicsJournal of







Biomaterials




Journal of


Journal of





CoatingsJournal of

Advances in








MaterialsJournal of


Nano

materials




H N

O

(xxxi)

21913 2196 21921

+

NH2

R2

R2

R2

R1R1




O

O

+OHC

O

OO

NH

O

O

O(xxxii)

21918 21922 2162 21923

21924


OCH2Ph

OCH2Ph

OCH2Ph

OCH2Ph+ +NH4OAC







2-



2








O

O

OH

O

O

NH

O

COOH21925 21926

21927

R1

R1

R2

R2

R2

R2

NH4OAc

R1 = Cl OCH3

R2 = H Me

+ +

CH3

TiO2 NPs


Y

XH

Y

X

HN O

2201 2202 2203

(xxxiii)


NH2

+ RO2C CO2R

CO2R

X = S O NHR = CH3

Y = CH N C2H5


O OMeMeON

R

R

O O

X

+N

N

X(xxxiv)

2211 22122213

2214 2215 2216

(xxxiv)


NH2

+


NHNH2

X = H Et ClR1

R1

= MemiddotOEt


INHR

R

2221 22222223

(xxxv)

(xxxv) 3 PdMIL-101

NH2

+



2231 2232

2233

N

O

N

OH

(xxxvi)


R1

R1

R2

R2

R3

R4

R4

R3

R5

R5


R4 = H Et


R6

R6

R7

R7

+


R OR

OHR

Cl

N

N

O

N O

a

b

c

R

R

N

OEt

R

O

O

Cl

(xxxvii)2234 2235 2236

2237

2238

2239N Cl N Cl

NaBH4 SOCl2


R =










N Cl

CHO

N Cl

OH

22310 22311

(xxxviii)



HN O

OCl RCl

N O

O

Cl

R

Cl

X

22312 2231422313

(xxxix)+

R =

X = CH3 OCH3




3F(H2O)2O(bdc)







3 Conclusions



N

NH

N

Cl

Cl N

N

NCl

O

22315 22316 22317

O

(XL)


+



Acknowledgments


References



















































2nanoparticles































2O4nano par-















2nanoparticles








4rdquo
























2O3)-MCM-41-SO
















3Has a green nano



















2nanopow-























CeramicsJournal of







Biomaterials




Journal of


Journal of





CoatingsJournal of

Advances in








MaterialsJournal of


Nano

materials




O

O

OH

O

O

NH

O

COOH21925 21926

21927

R1

R1

R2

R2

R2

R2

NH4OAc

R1 = Cl OCH3

R2 = H Me

+ +

CH3

TiO2 NPs


Y

XH

Y

X

HN O

2201 2202 2203

(xxxiii)


NH2

+ RO2C CO2R

CO2R

X = S O NHR = CH3

Y = CH N C2H5


O OMeMeON

R

R

O O

X

+N

N

X(xxxiv)

2211 22122213

2214 2215 2216

(xxxiv)


NH2

+


NHNH2

X = H Et ClR1

R1

= MemiddotOEt


INHR

R

2221 22222223

(xxxv)

(xxxv) 3 PdMIL-101

NH2

+



2231 2232

2233

N

O

N

OH

(xxxvi)


R1

R1

R2

R2

R3

R4

R4

R3

R5

R5


R4 = H Et


R6

R6

R7

R7

+


R OR

OHR

Cl

N

N

O

N O

a

b

c

R

R

N

OEt

R

O

O

Cl

(xxxvii)2234 2235 2236

2237

2238

2239N Cl N Cl

NaBH4 SOCl2


R =










N Cl

CHO

N Cl

OH

22310 22311

(xxxviii)



HN O

OCl RCl

N O

O

Cl

R

Cl

X

22312 2231422313

(xxxix)+

R =

X = CH3 OCH3




3F(H2O)2O(bdc)







3 Conclusions



N

NH

N

Cl

Cl N

N

NCl

O

22315 22316 22317

O

(XL)


+



Acknowledgments


References



















































2nanoparticles































2O4nano par-















2nanoparticles








4rdquo
























2O3)-MCM-41-SO
















3Has a green nano



















2nanopow-























CeramicsJournal of







Biomaterials




Journal of


Journal of





CoatingsJournal of

Advances in








MaterialsJournal of


Nano

materials




2231 2232

2233

N

O

N

OH

(xxxvi)


R1

R1

R2

R2

R3

R4

R4

R3

R5

R5


R4 = H Et


R6

R6

R7

R7

+


R OR

OHR

Cl

N

N

O

N O

a

b

c

R

R

N

OEt

R

O

O

Cl

(xxxvii)2234 2235 2236

2237

2238

2239N Cl N Cl

NaBH4 SOCl2


R =










N Cl

CHO

N Cl

OH

22310 22311

(xxxviii)



HN O

OCl RCl

N O

O

Cl

R

Cl

X

22312 2231422313

(xxxix)+

R =

X = CH3 OCH3




3F(H2O)2O(bdc)







3 Conclusions



N

NH

N

Cl

Cl N

N

NCl

O

22315 22316 22317

O

(XL)


+



Acknowledgments


References



















































2nanoparticles































2O4nano par-















2nanoparticles








4rdquo
























2O3)-MCM-41-SO
















3Has a green nano



















2nanopow-























CeramicsJournal of







Biomaterials




Journal of


Journal of





CoatingsJournal of

Advances in








MaterialsJournal of


Nano

materials




N Cl

CHO

N Cl

OH

22310 22311

(xxxviii)



HN O

OCl RCl

N O

O

Cl

R

Cl

X

22312 2231422313

(xxxix)+

R =

X = CH3 OCH3




3F(H2O)2O(bdc)







3 Conclusions



N

NH

N

Cl

Cl N

N

NCl

O

22315 22316 22317

O

(XL)


+



Acknowledgments


References



















































2nanoparticles































2O4nano par-















2nanoparticles








4rdquo
























2O3)-MCM-41-SO
















3Has a green nano



















2nanopow-























CeramicsJournal of







Biomaterials




Journal of


Journal of





CoatingsJournal of

Advances in








MaterialsJournal of


Nano

materials




N

NH

N

Cl

Cl N

N

NCl

O

22315 22316 22317

O

(XL)


+



Acknowledgments


References



















































2nanoparticles































2O4nano par-















2nanoparticles








4rdquo
























2O3)-MCM-41-SO
















3Has a green nano



















2nanopow-























CeramicsJournal of







Biomaterials




Journal of


Journal of





CoatingsJournal of

Advances in








MaterialsJournal of


Nano

materials
































2nanoparticles































2O4nano par-















2nanoparticles








4rdquo
























2O3)-MCM-41-SO
















3Has a green nano



















2nanopow-























CeramicsJournal of







Biomaterials




Journal of


Journal of





CoatingsJournal of

Advances in








MaterialsJournal of


Nano

materials

















2O4nano par-















2nanoparticles








4rdquo
























2O3)-MCM-41-SO
















3Has a green nano



















2nanopow-























CeramicsJournal of







Biomaterials




Journal of


Journal of





CoatingsJournal of

Advances in








MaterialsJournal of


Nano

materials





















2O3)-MCM-41-SO
















3Has a green nano



















2nanopow-























CeramicsJournal of







Biomaterials




Journal of


Journal of





CoatingsJournal of

Advances in








MaterialsJournal of


Nano

materials








2nanopow-























CeramicsJournal of







Biomaterials




Journal of


Journal of





CoatingsJournal of

Advances in








MaterialsJournal of


Nano

materials










CeramicsJournal of







Biomaterials




Journal of


Journal of





CoatingsJournal of

Advances in








MaterialsJournal of


Nano

materials



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Review Article Function of Nanocatalyst in Chemistry of Organic Compounds Revolution ...downloads.hindawi.com/journals/jnm/2013/341015.pdf · 2019-07-31 · Review Article Function