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A synthesis of lumazine derivatives
Author(s) -
Yoneda Fumio,
Koga Ryosuke,
Nishigaki Sadao,
Fukazawa Shinobu
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.5570190452
Subject(s) - chemistry , dimethyl acetylenedicarboxylate , thionyl chloride , dimethylformamide , ammonia , hydrolysis , medicinal chemistry , hydrochloric acid , chloride , organic chemistry , catalysis , solvent , cycloaddition
Treatment of 6‐amino‐1,3‐dimethyl‐5‐nitrosouracil (Ia) with dimethyl acetylenedicarboxylate (DMAD) in dimethylformamide (DMF) afforded 6,7‐bis(dimethoxycarbonyl)‐1,3‐dimethyllumazine (II). Similarly, the reaction of 6‐amino‐1,3‐dimethyl‐5‐phenylazouracil with DMAD gave also II. Hydrolysis of II with hydrochloric acid gave 1,3‐dimethyllumazine‐6‐carboxylic acid (III). III was chlorinated with thionyl chloride and then aminated with ethanolic ammonia to give rise to 6‐carbamoyl‐1,3‐dimethyllumazine (V). V was alternatively synthesized by the treatment of Ia with propiolamide in DMF.