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Pyrimidines. LII Synthesis of pyrido[2,3‐d]pyrimidine‐2,4‐diones and pyrido[2,3‐d:6,5‐d']dipyrimidine‐2,4,6,8‐tetrones
Author(s) -
Hirota Kosaku,
Kitade Yukio,
Senda Shigeo
Publication year - 1985
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.5570220224
Subject(s) - chemistry , malononitrile , barbituric acid , pyrimidine , methylene , triethylamine , hydrochloride , ethyl cyanoacetate , medicinal chemistry , stereochemistry , organic chemistry , catalysis
Reactivities of 5‐dimethylaminomethylene‐6‐imino‐1,3‐dimethyluracil hydrochloride ( 1 ) toward a variety of active methylene compounds 2 and 5 were investigated. Treatment of 1 with active methylene compounds such as malononitrile and ethyl cyanoacetate in the presence of triethylamine gave pyrido[2,3‐ d ]pyrimidine‐2,4‐dione derivatives 3. Reaction of 1 with barbituric acids resulted in the formation of pyrido[2,3‐ d :6,5‐ d ′]di‐pyrimidine‐2,4,6,8‐tetrone derivatives 6.