Problemas de Organica Resueltos

8/12/2019 Problemas de Organica Resueltos

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!"##$%&$' %)*"&+),% -). /012&$. 34

56789:; <"#$$%&' ( )%*+(,-&) ./0 '+-& &1,'+%&-& /. ( '0-*1*2-* (0/)('-* +%'%0/*1*2%3

N

NH 2

Cl

O

+base

N

HN

5".2)%$ )- &0$ 2.)=*$>

4 &-)52% %6%0*-&% -, '+% &1,'+%&-& /. ( 510-7-,% .#&%7 '/ ( 5100/2% 8/0 (,-,7/2% 9-'+ (, %6'0( ,-'0/$%, ('/):3

!"##$%&$' %)*"&+),

;+% .-0&' &'%5 )#&' <% '+% ./0)('-/, /. (, %,()-,% <%'9%%, '+%50-)(01 ()-,% (,7 '+% =%'/,%3 >/9? <%*(#&% 9% +(@% ( 510-7-,% (,7,/' ( <%,A%,% 0-,$? ,#*2%/5+-2-* (0/)('-* &#<&'-'#'-/, *(, /**#03 ;+%&%B(A(C-,7/2%&D (0% )/0% %(&-21 ./0)%7 '+(, -,7/2%&3

N

NH 2

Cl

O

N

N

Cl

H

N

N

Cl

H

N

N

H

HN

HN

EF



? "/2#'-/,& G(,#(2 '/ (**/)5(,1 H0$(,-* I+%)-&'01 J%

56789:; ?K& '+% +%'%0/*1*2-* 0-,$ *0%('%7 -, '+-& 0%(*'-/, (0/)('-*L M/9 7/%& '+% 0%(*'-/,50/*%%7L I/))%,' /, '+% 0%$-/&%2%*'-@-'1 /. '+-& *1*2-&('-/,3

OOHHO

CO 2 Et

O

H 2 SO 4 HO O

5".2)%$ )- &0$ 2.)=*$>

N652/0-,$ '+% &1,'+%&-& (,7 (0/)('-*-'1 /. (, #,.()-2-(0 +%'%0/*1*2%3

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OHO O

a ten-electron ! system

OHO O OHO O

;+% .-0&' &'%5 -, '+% 0%(*'-/, -& ( '0(,&%&'%0-.-*('-/, (,7 *1*2-A('-/,'+%, /**#0& -, '+% !"#$! 5/&-'-/,? %&"&'/ '+% /'+%0 +170/612 $0/#53I1*2-A('-/, )-$+' +(@% +(55%,%7 '/ '+% 5/&-'-/, -, <%'9%%, '+% '9/&#<&'-'#%,'&? (& '+% /'+%0 HM -&!"#$!( %&"&C7-0%*'-,$? <#' '+% 5/&-'-/,*+/&%, -& )/0% 0%(*'-@% ./0 </'+ &'%0-* (,7 %2%*'0/,-* 0%(&/,&3

OHHO

CO 2 Et

O

H 2 SO 4OHO O

O H

OHO O

H OH

H

OHO O

OH

OHO O

OH

H

E1cB

OHO O

! ;+-& -& ( @%01 /27 0%(*'-/,7-&*/@%0%7 <1 M3 @/, R%*+)(,,(,7 I3 S#-&<%0$? )*"+? OTTE? JOOU3

! "%% 53 VTE /. '+% '%6'<//= ./0)/0% /, '+% &%2%*'-@-'1 <%'9%%,'+% !"#$! (,7 %&"& 5/&-'-/,&3



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O

NNHPh

HCl

N

O

ZnCl 2

NH

NO

5".2)%$ )- &0$ 2.)=*$>

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!"##$%&$' %)*"&+),

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N

O

HN NH

N

O

NHNH

H

H

HCl

N

O

NH 2

NHH

NH

N

O

NH 2

H

N

N

O

NH 3

HN

N

O

;0%(')%,' 9-'+ ( _%9-& (*-7 -,-'-('%& ( 0%(00(,$%)%,' @%01 2-=% '+/&%/**#00-,$ 9+%, EC&#<&'-'#'%7 -,7/2%& (0% (''(*=%7 <1 %2%*'0/5+-2%& 853YVZ:3 ;+% (0/)('-* 0-,$ -& ( <%''%0 )-$0('-,$ $0/#5 '+(, '+% 50-)(01(2=12 (2'%0,('-@% (,7 (, -,7/2% *(, .-,(221 <% ./0)%73



@ "/2#'-/,& G(,#(2 '/ (**/)5(,1 H0$(,-* I+%)-&'01 J%

N

N

O

ZnCl 2

N

N

O

ZnCl 2

H NH

N

O

56789:; @N652(-, '+% 0%(*'-/,& -, '+-& 5(0'-(2 &1,'+%&-& /. )%'+/6('-,? '+%*/%,A1)% /. <(*'%0-( 2-@-,$ /, )%'+(,/23

NH2

NHCHO

OMe

1. HONO

2. KOH,

O

CO 2Me

NH

NHCHO

OMe

NMeO 2C

HCO 2H

80 °C

NHCHO

OMe

NH

MeO 2C

HCl, H 2OMe 2C=O

NH 2

OMe

NH

MeO 2C

CO 2Me

CO 2MeO N

OMe

NH

MeO 2C

CO 2Me

CO 2Me

+

5".2)%$ )- &0$ 2.)=*$>

4 */)<-,('-/, /. [-&*+%0 -,7/2% &1,'+%&-& 9-'+ 0%@-&-/, /. -,7/2%*+%)-&'01 .0/) *+(5'%0 JU3

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! ;+% ,%9 &%@%,C)%,<%0%7+%'%0/*1*2% 8(, (A%5-,%: -& ./#,7-, &/)% '0(,^#-2-A%0&X &%% ;3 "3 ;3`(,$? .*#"&$*/"!0 1*##+ ? OUYa?OZEY3

! S-(A/'-A('-/,X &%% 53 aJO /. '+%'%6'<//=3





B "/2#'-/,& G(,#(2 '/ (**/)5(,1 H0$(,-* I+%)-&'01 J%

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N

Ph O

KOH, H 2ONH 2

O

Ph O

H2SO 4 , HOAcN

Ph

5".2)%$ )- &0$ 2.)=*$>

4, %6%0*-&% -, 0%$-/&%2%*'-@-'1 -, ( +%'%0/*1*2-* &1,'+%&-& */,'0/22%7 <15M3

!"##$%&$' %)*"&+),

b/# +(@% ( *+/-*% +%0%X %-'+%0 1/# .-0&' ./0) (, %,/28('%: .0/)<#'(,/,% (,7 7/ (, (27/2 0%(*'-/, 9-'+ '+% (0/)('-* =%'/,% /0 1/# .-0&')(=% (, -)-,% (,7 '+%, ./0) %,()-,%& .0/) '+('3 K, %-'+%0 *(&%? 1/#9/#27 %65%*' %,/2 /0 %,()-,% ./0)('-/, /, '+% )/0% &#<&'-'#'%7 &-7%-, (*-7 <#' '+% 2%&& &#<&'-'#'%7 &-7% -, <(&%3

OKOH, H 2O H2SO 4, HOAc OHO

N

O

Ph

H2SO 4 , HOAc

NH

O

Ph

KOH, H 2O

NH

O

Ph

! ;+-& &%2%*'-@% 0/#'% '/^#-,/2-,%& <1 '+% [0-%72f,7%0&1,'+%&-& 9(& 7-&*/@%0%7 <1 N3 43[%+,%2? 2+ 3"4+ 5$*6+? OUZZ?3< ?JTUU3



"/2#'-/,& ./0 I+(5'%0 EF W 40/)('-* M%'%0/*1*2%& JX "1,'+%&-& C

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N

Me

Ph

O O

O+

HCl

dry Et 2O

O O

ON

Me

Ph

H

NH2OHHCl

EtOHNN

Me

Ph

H

5".2)%$ )- &0$ 2.)=*$>

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!"##$%&$' %)*"&+),

;+% .-0&' &'(0'-,$ )('%0-(2 -& ( &'(<2% *1*2-* %,()-,% (,7 */,]#$('%(77-'-/, -& 9+(' 9% &+/#27 %65%*' 9-'+ (, %,/,%3 H. */#0&%? -. '+%(27%+17% 9%0% #,50/'%*'%7? 7-0%*' (77-'-/, )-$+' /**#0 '+%0% (& 9%22 (&*(0</,12 */,7%,&('-/,&3 ;+% 50/7#*' -& -, %^#-2-<0-#) 9-'+ </'+ -'&%,/2&? /,% /. 9+-*+ *(, *1*2-A% '/ ./0) '+% ,%9 &-6C)%)<%0%7 0-,$3

N

Me

Ph

O O

OH

O O

OHN

Me

Ph

O O

ON

Me

Ph

O O

OHN

Me

Ph

O O

OHN

Me

Ph

H

O O

ON

Me

Ph

H





"/2#'-/,& ./0 I+(5'%0 EF W 40/)('-* M%'%0/*1*2%& JX "1,'+%&-& E

5".2)%$ )- &0$ 2.)=*$>

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!"##$%&$' %)*"&+),

;+% .-0&' 0%(*'-/, ./0)& 4? ]#&' '+% %,()-,% .0/) '+% =%'/,% (,7 '+%&%*/,7(01 ()-,% 8)/05+/2-,%:3 j%2/9 9% +(@% 7-(A/'-A('-/, /. (,(0/)('-* ()-,% (,7 0%52(*%)%,' <1 (A-7% '/ $-@% j3 ;+-& ,#*2%/5+-2-*&#<&'-'#'-/, */#27 /**#0 <1 '+% (77-'-/,C%2-)-,('-/, )%*+(,-&)(*'-@('%7 <1 '+% ,-'0/ $0/#5 /0 <1 '+% " > O )%*+(,-&) 8*+(5'%0 JJ:3

NH

OO

+ cat. H N

O

AC 10 H 17 NO

NH 2

NO 2

NaNO 2

HCl

N

NO 2

N

NaN 3

NaOAc

N 3

NO 2

BC 6 H 4 N 4 O 2

>/9 */)%& '+% -,'%0%&'-,$ <-'3 ;+% '9/ 0%($%,'& 4 (,7 j */)<-,%9-'+/#' 2/&-,$ (,1'+-,$ W -' -& %@-7%,' '+(' '+% %,()-,% )#&' <% '+%,#*2%/5+-2% (,7 &/ '+% (A-7% )#&' <% '+% %2%*'0/5+-2%3 `% *(, &%% .0/)'+% .-,(2 50/7#*' '+(' '+% %,()-,% (''(*=& /,% %,7 /0 '+% /'+%0 /. '+%(A-7%3 ;0-(2 (,7 %00/0 '(=%& /@%0k M%0% -& /,% 5/&&-<2% &/2#'-/, 9-'+&/)% &-7% *+(-,& -, '+% -,'%0)%7-('% (<<0%@-('%7 ./0 *2(0-'13 ;+-&50/7#*' / *(, <% -&/2('%7 <#' -'& &'%0%/*+%)-&'01 -& ,/' =,/9,3

N

O

N

NO 2

N

N

R 2 N

N

NN

Ar

N

N

N

NO 2

N

O

C

[-,(221? '+% ,%9 (0/)('-* &1&'%) 8( '0-(A/2%: -& ./0)%7 <1 %2-)-,('-/,/. '+% ()-,(23 R0/'/,('-/, /. '+% )/&' <(&-* ,-'0/$%, -& ./22/9%7 <1%65#2&-/, /. )/05+/2-,% (,7 (0/)('-A('-/, <1 7%50/'/,('-/,3

! 4, (2'%0,('-@% -& ( O?EC7-5/2(0*1*2/(77-'-/,? &%% *+(5'%0 EV3

! ;+-& &1,'+%&-& 9(& 7-&*/@%0%7-, G-2(, 7#0-,$ ( )%*+(,-&'-* &'#71/. '+% 0%(*'-/,& <%'9%%, %,()-,%&(,7 (A-7%&X i3 [#&*/ %' (23 ( 8&99+5$-6+ :#&;+? OUZO?E<? TVU3





"/2#'-/,& ./0 I+(5'%0 EF W 40/)('-* M%'%0/*1*2%& JX "1,'+%&-& <<

56789:; E"#$$%&' ( &1,'+%&-& ./0 '+-& */)5/#,73

NH

CO 2 MeMeO

MeO

NHPh

5".2)%$ )- &0$ 2.)=*$>

;+% &1,'+%&-& /. (, -,7/2% 9-'+ ( &2-$+' '9-&'3

!"##$%&$' %)*"&+),

;+-& 2//=& @%01 )#*+ 2-=% ( 5%0.%*' &#<]%*' ./0 '+% [-&*+%0 -,7/2%&1,'+%&-&3 _%'D& &%%3

NH

CO 2 Me

MeO

ClH

Fischerindole MeO

MeO NH

NH 2

CO 2 Me

NHPh

ONHPh

;+-& 2//=& .-,%? '+/#$+ 9% )(1 9/,7%0 +/9 9% (0% $/-,$ '/ +(@% (,

()-,/ $0/#5 -, '+(' 5/&-'-/, /, '+% =%'/ %&'%03 "#0%21 -' 9-22 *1*2-A% /,'/'+% %&'%0 '/ ./0) ( 2(*'()L H,% &/2#'-/, 9/#27 <% '/ 50/'%*' -' 9-'+&/)%'+-,$ 2-=% ( j/* $0/#5? <#' '+% &/2#'-/, ./#,7 <1 '+% "'%02-,$ S0#$*/)5(,1 9(& 5(0'21 )/'-@('%7 <1 ( 7%&-0% '/ )(=% ( @(0-%'1 /.*/)5/#,7& 9-'+ 7-..%0%,' ()-,%& &#<&'-'#%,'&3 ;+%1 *+/&% +170/612 (&(, %(&-21 0%52(*%(<2% $0/#5 (,7 (**%5'%7 '+(' '+% &'(0'-,$ )('%0-(29/#27 %6-&' (& ( 2(*'/,%3 ;+%1 )(7% -' 2-=% '+-&X

O O

CO 2 Et

CO 2 Et

EtO O O

CO 2 Et

O

H 2 SO 4

O

CO 2 Et

O

O O

O

O

;+% .-0&' &'%5 -& ( '15-*(2 I2(-&%, %&'%0 */,7%,&('-/, (,7 '+% &%*/,7 -&(, (*-7C*('(21&%7 '+%0)/71,()-*(221 */,'0/22%7 '0(,&%&'%0-.-*('-/, 8'+%2(*'/,% (,7 %'+12 %&'%0 %6*+(,$% (2*/+/2 5(0',%0&: '/ $-@% '+% )/0%&'(<2% &-6C)%)<%0%7 2(*'/,%? ./22/9%7 <1 7%*(0</612('-/,3 >/9 '+%[-&*+%0 -,7/2% &1,'+%&-& 9/0=& 9%22 (,7 9/0=C#5 9-'+ 701 MI2 -,





"/2#'-/,& ./0 I+(5'%0 EF W 40/)('-* M%'%0/*1*2%& JX "1,'+%&-& <3

IW" </,7& '/ $-@% '+% '+-/()-7% (,7 (,/'+%0 ! C<0/)/=%'/,%0%)%)<%0-,$ '/ 2%' '+% ,#*2%/5+-2%& %6%0*-&% '+%-0 ,('#0(2 50%.%0%,*%&X&#2.#0 (''(*=-,$ &('#0('%7 *(0</, (,7 ,-'0/$%, (''(*=-,$ '+% *(0</,12$0/#53

analysis

synthesis

S

NPh

C–N + C–S

Ph+

O

Br

H 2 N

S C–BrPh

O

Ph

O

Br 2

HOAc Ph

O

BrH 2 N

S

S

NPh

;+% '+-07 */)5/#,7 +(& '+% '9/ +%'%0/('/)& ]/-,%7 '/$%'+%0 &/ 9%&+/#27 =%%5 '+%) '+(' 9(13 `% 7-&*/,,%*' </'+ IW> </,7& 0%@%(2-,$'+% +-77%, )/2%*#2% /. +170(A-,% 8>M J >MJ :3 `% '+%, ,%%7 ( O?EC7-=%'/,% &/ 9% ,%%7 I2(-&%, %&'%0 *+%)-&'01 8*+(5'%0 JZ:3

analysis

synthesis

NHN

Ph

2 x C–NH 2 N NH 2

Ph

O O1,3-diCO

Ph

O O

X+

+

Ph

OMe 3 SiCl

Et 3 N Ph

OSiMe 3

O

X

TiCl 4

Ph

O O H 2 N NH 2 NHN

Ph

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Problemas de Organica Resueltos