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Studies on Condensed Triazines and Related Compounds
Author(s) -
Ram Vishnu Ji
Publication year - 1979
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.19793120212
Subject(s) - chemistry , ethyl acetoacetate , acetylacetone , formic acid , triazine , hydrazine (antidepressant) , alkyl , medicinal chemistry , nitrous acid , tetrazole , nucleophile , derivative (finance) , halide , hydrazide , organic chemistry , catalysis , chromatography , financial economics , economics
Acenaphthone monosemicarbazone was cyclised to acenaphtheno[1,2‐ ‐e ]1,2,4‐triazine‐3‐one ( 2 ). Its N ‐alkyl derivative 3 was prepared by the reaction with an alkyl halide in alkaline medium. The triazinone 2 was further converted into the corresponding chloro compound 4 which underwent nucleophilic substitutions with hydrazine and amines. 3‐Hydrazinoacenaphtheno[1,2‐ e ]‐1,2,4‐triazine ( 9 ) was transformed into pyrazolotriazines 12, 13, 14 by reaction with acetylacetone, ethyl acetoacetate and ethyl ethoxymethylenecyanoacetate. With formic acid and nitrous acid 9 yielded the new heterocycles acenaphtheno [1,2‐ e ]‐1,2,4‐triazino[2,3‐ d ]‐1,2,4‐triazole ( 11 ) and acenaphtheno[1,2‐ e ]‐1,2,4‐triazino[2,3‐ d ]‐tetrazole ( 10 ).