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Anntbaudaa S.

u s e d helocyele

Eeuzopyroles- (TNDOLE)
Beu2ene otng tused to the d.B -Po8tion) oa
Prrole seng
Solubl n Cold oater
Spareugly

Poeparration
ta
O teshev Iudole Suthe stu- Tu thu nettho d phenylhyra2ne

t stoeoctec otm Potv?c cactd to Jorm Cosresponden henyl


The hydo3one tton toeated otm 2nc Ehlotde,
hydopne
tndole
acrd ohte h on de Coborylatton gfues
to gtve -Caslooryltt

+
-OH Znc N

O -C0
phenylhydraztne PYTuvt cacrd
Treale

Ret&8eot Smihesu

CH2 + o - - -ocH -cH-

ND2
O- nttov- touleue drethylotalate t e ste%

Zn CHCODH

CH-. -oH
-OH
2
Tudole unsHable
Sudol-9- Corrooxylkt actd
lectrophtlte Substtution-ndole underqoct substitatiirn å c2
dtate Cation,
bc2 fuoo etonance torma Can be orttHen ostntrme
obtane -Jsom d C3 crtta tk wtthout destnbeng Beurene
otng.
e as only one Such ovm u poAstle ot

At C2

H 3-Subshitutd prdud
more sta ble

At C
H
H
lecd StaLle -Sub stitukd

move mOre ayo b veason


C3
Nthoq en (e Lushoneq ctihe) qei +vechoay
re10nante poMble
Reatfong

OWthrat eon
NO
-
+SMONa

3 - n i t r ofndou ,

Suphonaho n

Presliu L
Judole 3-Su ontt acid.
Brornenat?on:
Br
D:020
H

3-Bromo -Iudole

ttdel Cralt acyatton

+Ch-ct. Snct K
aeetyl chlonv:ds
-ae etyl-tndole

Beu2ouron-
Symtests
CHO
CHO
CICHcoot. NaoH
oH ++ 6-CHcooH.
0-hyarox-Beunaldehyele
ChLoateticacid
Aaceticanhydmde Sodtumaetate
AO,HoAC. Ala0Ac

Benzo"
Eleetopheltc substitution i- (C- pos:tion

+ HNO3
Y-nttoben2o{uYon
N

Bromtmathon
Bo-B BB

B
pop-2-eh-ehor.
Clasan oeaorangement,. goyl-2-chloro
Synthestuom

K
aryl-2-chlonprop 2-n-eher.

methyl-ben2ouau

Ben2gtktophene-
CH=CH-Cl
ALLoheltt koH
SH
Ben2othroph ene
-mesapto B-Cklonstyrene.
-
wtth chlontthylatttate
tollos ed by
p Peaction sf s alicyldehyde. Ben2othtophnr.
and decoboxylaHon yetdf to
Cycltzation
Mh

Cl-CH-(oo Et
K -OH
o-cH-C0DE+

Cot
c00EE

C0

Ben2auno
Beu 01iopheue by oylthioatettc actd -

Aryoacette acrd on (ychzation provde 3-hydroy


e
24htophene toht ch on doeotment wtth 2n] CHlUDH qtves ben2othiophe

halthtotetkaetd.
0
HO -OH
Zn Ctay
M

Electooph?lre Subs ituton *-


C3tavoT C3

C
0nqdetuvb
t c e k p l e L C e

NO3
HNO,/A0

So, Pyridua
utnoene Ceulrral ornmwlo

0 SEaup eation
AQ y(ghevol)

N N
sO PhNO

Doebnes rece tion

R-CHO

HO

Electropheltc Subshtution- ESe at C.C


LSR at C

NO

HO3

H,&O4 +

soM
8

Cont O4
Smestu

acetaldehyde
O-aninmobenalddhjd

AtSP at2

N
Sodaide

SnHu
Pesduehion .23Hethydaqunelene

eduthon decwhy doqunoltne

IsoguO LUNE

Fom CPuama ldehy de


O

Peavsanqcmusd

HfHN-OH CN-0H Cyckratio


4P,0
Cnamaldthyde
hydroxy H
ISoqunoltne.
.CH
CH2
+

KDorgare
mesrt
2 yclrati
phenyl eth fomylchlontde
amtne ,

ISoquneltne.

ES Cs

Sam eaction3

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