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Studies on Condensed Triazines as Chemotherapeutic Agents, II. Synthesis of 1,2,4‐Triazino[5,6‐ b ]indoles and Related Compounds
Author(s) -
Ram Vishnu Ji
Publication year - 1980
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.19803130203
Subject(s) - chemistry , isatin , acetylacetone , hydrazine (antidepressant) , yield (engineering) , formic acid , medicinal chemistry , indole test , hydrazone , semicarbazone , acetic anhydride , organic chemistry , catalysis , materials science , chromatography , metallurgy
1,2,4‐Triazino[5,6‐ b ]indoles and their derivatives are prepared by the cyclisation of isatin 3‐thiosemicarbazone (1) followed by condensation and displacement reactions. Condensations of 3‐hydrazino‐1,2,4‐triazino[5,6‐ b ]indole (4) with ethoxymethylenemalononitrile, ethyl ethoxymethylenecyanoacetate, acetylacetone and methyl bis(methylmercapto)methylenecyanoacetate yield the corresponding 3‐pyrazolo‐1,2,4‐triazino[5,6‐b]indoles 6–9. The hydrazine 4 is further transformed into the higher heterocycles 10–12 on reaction with formic, acetic or nitrous acids.