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Methyl 2‐benzoylamino‐3‐dimethylaminopropenoate in the synthesis of heterocyclic systems. The synthesis of benzoyl‐ amino substituted 7 H ‐pyrano[2,3‐ d ]pyrimidine, 1 H ,6 H ‐pyrano‐ [2,3‐ c ]pyrazole and 2 H ‐1‐benzopyran derivatives
Author(s) -
Stanovnik Branko,
Svete Jurij,
Tišler Miha
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.5570260511
Subject(s) - chemistry , barbituric acid , resorcinol , methylene , pyrimidine , pyrazolones , acetic acid , ring (chemistry) , organic chemistry , medicinal chemistry , stereochemistry
Methyl 2‐benzoylamino‐3‐dimethylaminopropenoate (6) reacts with heterocyclic compounds containing an active methylene group or potential methylene group in the ring system, such as barbituric acid derivatives 1 and 2, pyrazolones 3 and 4, and resorcinol, in acetic acid to afford the corresponding benzoylamino substituted pyranopyrimidinones 7 and 8 , pyranopyrazolones 9 and 10 , and 2 H ‐1‐benzopyranone 11 . The method represents a novel procedure for the preparation of condensed pyranones.