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Cyclization reactions of 3‐hydrazino[1, 2, 4]triazino[5, 6‐ b ]indole
Author(s) -
AbdelLatif F. F.,
Shaker R. M.,
Mahgoub S. A.,
Badr M. Z. A.
Publication year - 1989
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570260348
Subject(s) - chemistry , ethyl acetoacetate , malononitrile , acetic anhydride , acetylacetone , ethyl chloroformate , medicinal chemistry , indole test , organic chemistry , acetic acid , nitrous acid , catalysis
The reaction of 3‐hydrazino[1, 2, 4]triazino[5, 6‐ b ]indole I with nitrous acid affords the azide III which could be cyclized with acetic anhydride to 10‐acetyl‐10 H ‐tetrazolo[5′,1′:3, 4][1, 2, 4]triazino[5, 6‐ b ]indole IIb . Cyclization reactions of I with acetic anhydride, ethyl chloroformate, carbon disulphide and aromatic aldehydes to the corresponding fused triazolo derivatives V–VIII are reported. On the other hand cyclization reactions of I with malononitrile, ethyl cyanoacetate, ethyl acetoacetate and acetylacetone to the corresponding condensed pyrazolino derivatives IX–XI are also reported. The reaction of I with α‐dicarbonyl compounds to form mono and dihydrazones are reported. The structure of the compounds prepared and their cyclization mechanisms are reported.