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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
+
-OH Znc N
O -C0
phenylhydraztne PYTuvt cacrd
Treale
Ret&8eot Smihesu
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
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
+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 -
halthtotetkaetd.
0
HO -OH
Zn Ctay
M
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
R-CHO
HO
NO
HO3
H,&O4 +
soM
8
Cont O4
Smestu
acetaldehyde
O-aninmobenalddhjd
AtSP at2
N
Sodaide
SnHu
Pesduehion .23Hethydaqunelene
IsoguO LUNE
Peavsanqcmusd
KDorgare
mesrt
2 yclrati
phenyl eth fomylchlontde
amtne ,
ISoquneltne.
ES Cs
Sam eaction3