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Construction of pyrimido[5,4‐ e ]‐ as ‐triazine, purine, v ‐triazolo‐[4,5‐ d ]pyrimidine and pyrazolo[3,4‐ d ]pyrimidine ring systems from 5‐arylazo‐6‐arylidenehydrazino‐1,3‐dimethyluracils
Author(s) -
Nishigaki Sadao,
Ichiba Misuzu,
Fukami Kiyoko,
Senga Keitaro
Publication year - 1982
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.5570190413
Subject(s) - chemistry , pyrimidine , triazine , ring (chemistry) , purine , dimethylformamide , aryl , stereochemistry , medicinal chemistry , d 1 , organic chemistry , enzyme , solvent , biochemistry , alkyl , receptor
Reaction of 5‐arylazo‐6‐arylidenehydrazino‐1,3‐dimethyluracils (II), prepared by the treatment of 6‐aryl‐idenehydrazino‐1,3‐dimethyluracils (I) with diazotized arylamines, with dimethylformamide dimethylacetal resulted in the formation of pyrimido[5,4‐ e ]‐ as ‐triazine (V) system, while the thermolysis of II resulted in the formation of purine (X), v ‐triazolo[4,5‐ d ]pyrimidine (XII), and pyrazolo[3,4‐ d ]pyrimidine (XIV, XIX) systems in lieu of the expected V. Reasonable mechanisms have been proposed for the formation of the various ring systems in these reactions.