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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
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? "/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
!"##$%&$' %)*"&+),;+% 2%.'C+(,7 0-,$ -& /<@-/#&21 (0/)('-* (& -' -& ( <%,A%,% 0-,$3 ;+%0-$+'C+(,7 0-,$ +(& ./#0 %2%*'0/,& .0/) '+% 7/#<2% </,7& (,7 *(, +(@%'9/ .0/) ( 2/,% 5(-0 /, /61$%,? )(=-,$ &-6 -, (223 ;+-& -& )/0% /<@-/#&-, ( 7%2/*(2-&%7 ./0)3 42'%0,('-@%21 '+% 9+/2% &1&'%) *(, <% */,&-7%0%7(& ( OFC%2%*'0/, )/2%*#2%3 "'0(,$%21 %,/#$+? '+-& -& %(&-%0 '/ &%% -, '+%/'+%0 P%=#2Q ./0)3
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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"/2#'-/,& ./0 I+(5'%0 EF W 40/)('-* M%'%0/*1*2%& JX "1,'+%&-& 3
56789:; 3"#$$%&' )%*+(,-&)& ./0 '+-& #,#&#(2 -,7/2% &1,'+%&-&3 M/9 7/%& '+% &%*/,7)%*+(,-&) 0%2('% '/ %2%*'0/5+-2-* &#<&'-'#'-/, /, -,7/2%& 853 YVZ: L
O
NNHPh
HCl
N
O
ZnCl 2
NH
NO
5".2)%$ )- &0$ 2.)=*$>
4 */)<-,('-/, /. ( [-&*+%0 -,7/2% &1,'+%&-& 9-'+ 0%@-&-/, /. ( <-' /.-,7/2% *+%)-&'01 .0/) '+% 2(&' *+(5'%03
!"##$%&$' %)*"&+),
;+% .-0&' &'%5 &'(0'& /.. (& ( ,/0)(2 [-&*+%0 -,7/2% &1,'+%&-& 89% +(@%/)-''%7 '+% .-0&' &'%5:\ 1/# ]#&' +(@% '/ 70(9 '+% )/2%*#2%& *(0%.#221 '/&+/9 '+% ,%-"! 0-,$ &1&'%)? (,7 1/# +(@% '/ &'/5 <%./0% (, -,7/2% -&./0)%7 (& '+% ^#('%0,(01 *%,'0% 50%@%,'& (0/)('-A('-/,3
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 )-$0('-,$ $0/#5 '+(, '+% 50-)(01(2=12 (2'%0,('-@% (,7 (, -,7/2% *(, .-,(221 <% ./0)%73
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@ "/2#'-/,& G(,#(2 '/ (**/)5(,1 H0$(,-* 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.)=*$>
4 */)<-,('-/, /. [-&*+%0 -,7/2% &1,'+%&-& 9-'+ 0%@-&-/, /. -,7/2%*+%)-&'01 .0/) *+(5'%0 JU3
!"##$%&$' %)*"&+),
;+%0% -& *2%(021 ( [-&*+%0 -,7/2% &1,'+%&-& -, '+% &%*/,7 &'%5 <#' '+%
.-0&' &'%5 )(=%& '+% #&#(2 +170(A/,% -, ( )/&' #,#&#(2 9(13 ;+% .-0&'0%(*'-/, -& ( 7-(A/'-A('-/, &/ 9% +(@% '/ */)<-,% '+% 7-(A/,-#) &(2'9-'+ '+% %,/2('% /. '+% =%'/C%&'%03 ;+(' *0%('%& ( ^#('%0,(01 *%,'0% (,7'+% PHM 7%(*12('%& -' '/ $-@% '+% (012 +170(A/,% ,%%7%7 ./0 '+% ,%6'&'%53
! ;+% ,%9 &%@%,C)%,<%0%7+%'%0/*1*2% 8(, (A%5-,%: -& ./#,7-, &/)% '0(,^#-2-A%0&X &%% ;3 "3 ;3`(,$? .*#"&$*/"!0 1*##+ ? OUYa?OZEY3
! S-(A/'-A('-/,X &%% 53 aJO /. '+%'%6'<//=3
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B "/2#'-/,& G(,#(2 '/ (**/)5(,1 H0$(,-* I+%)-&'01 J%
56789:; AN652(-, 9+1 '+%&% '9/ ^#-,/2-,% &1,'+%&%& .0/) '+% &()% &'(0'-,$ )('%0-(2&$-@% 8)(-,21: 7-..%0%,' 50/7#*'&3
N
Ph O
KOH, H 2ONH 2
O
Ph O
H2SO 4 , HOAcN
Ph
5".2)%$ )- &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$*6+? OUZZ?3< ?JTUU3
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"/2#'-/,& ./0 I+(5'%0 EF W 40/)('-* M%'%0/*1*2%& JX "1,'+%&-& C
56789:; Bg-@% )%*+(,-&)& ./0 '+%&% 0%(*'-/,& #&%7 '/ 50%5(0% ( .#&%7 510-7-,%3 `+1 -& -',%*%&&(01 '/ #&% ( 50/'%*'-,$ $0/#5L
N
Me
Ph
O O
O+
HCl
dry Et 2O
O O
ON
Me
Ph
H
NH2OHHCl
EtOHNN
Me
Ph
H
5".2)%$ )- &0$ 2.)=*$>
"('#0('%7 (,7 (0/)('-* +%'%0/*1*2%& */)<-,%7 9-'+ &'%0%/*+%)-&'01)(=% (, -,'%0%&'-,$ &1,'+%&-& ./0 1/# '/ %652/0%3
!"##$%&$' %)*"&+),
;+% .-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-,$3
N
Me
Ph
O O
OH
O O
OHN
Me
Ph
O O
ON
Me
Ph
O O
OHN
Me
Ph
O O
OHN
Me
Ph
H
O O
ON
Me
Ph
H
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"/2#'-/,& ./0 I+(5'%0 EF W 40/)('-* M%'%0/*1*2%& JX "1,'+%&-& E
5".2)%$ )- &0$ 2.)=*$>
i%@-&-/, /. (0/)('-* ,#*2%/5+-2-* &#<&'-'#'-/, (,7 ( *+(,*% '/ #,0(@%2(, -,'%0%&'-,$ )%*+(,-&)3
!"##$%&$' %)*"&+),
;+% .-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
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"/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 -,
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"/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.#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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