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10‐Carbethoxymethyl‐3‐phenyl‐1,2,4‐triazolo[4′,3′:2,3][1,2,4]triazino[5,6‐ b ]indole and Derivatives at its 10‐Position
Author(s) -
Rashed Nagwa,
Nemr Ahmed El,
El Ashry El Sayed H.
Publication year - 1993
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19933260307
Subject(s) - chemistry , ethyl chloroacetate , indole test , acetylacetone , medicinal chemistry , methylhydrazine , hydrate , hydrazine (antidepressant) , hydrazone , acetophenone , ethyl acetoacetate , cyclohexanone , condensation reaction , stereochemistry , organic chemistry , catalysis , phenylhydrazine , chromatography
Reaction of 3‐phenyl‐10 H ‐1,2,4‐triazolo[4′,3′:2,3][1,2,4]triazino[5,6‐ b ]indole ( 4 ) with ethyl chloroacetate gave 10‐carbethoxymethyl‐3‐phenyl‐1,2,4‐triazolo[4′,3′:2,3][1,2,4]triazino[5,6‐ b ]indole ( 3 ). Condensation of 3 with hydrazine hydrate gave (3‐phenyl‐1,2,4‐triazolo[4′,3′:2,3][1,2,4]triazino[5,6‐ b ]indol‐10‐yl)acetylhydrazine ( 5 ). Reactions of 5 with a number of aromatic aldehydes, acetophenone, cyclohexanone and D‐galactose gave the corresponding hydrazones 6 ‐ 12 . Condensation of 5 with acetylacetone gave the pyrazole 15 . Cyclization of 5 with CS 2 gave (3‐phenyl‐1,2,4‐triazolo[4′,3′:2,3][1,2,4]triazino[5,6‐ b ]indol‐10‐yl)(2‐thiol‐1,3,4‐oxadiazol‐5‐yl)methane ( 16 ). Reaction of 16 with ethyl chloroacetate gave the carbethoxy alkylated derivative (3‐phenyl‐1,2,4‐triazolo[4′,3′:2,3][1,2,4]triazino[5,6‐ b ]indol‐10‐yl)[2‐(thiocarbethoxymethyl)1,3,4‐oxadiazol‐5‐yl]methane ( 17 ).
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