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Benzopyrans. Part 23. Nitrogen heterocycles fused with or linked to 1-benzopyran from 3-acyl-2-methyl-1-benzopyran-4-one
C K GHOSH, C PAL, J MAITI, M SARKAR
Published in Royal Society of Chemistry
1988
   
Issue: 6
Pages: 1489 - 1493
Abstract
The enamine (2), prepared from the title benzopyranone (1; R2 = H, Me, and Ph) and dimethylformamide dimethyl acetal, on treatment with ammonia and hydroxylamine gives the fused pyridine (5) and pyridine 2-oxide (10), respectively. Hydrazine, phenylhydrazine, and guanidine undergo initial 1,6-addition to the enamine (2) ultimately giving the pyrazoles (14) and (15), and the pyrimidine (17), respectively. The pyridinioacetamidate (11), prepared from the enamine (2; R2 = Me and Ph) and acetohydrazide, thermolyses to the fused pyridine (5). A refluxing ethanolic solution of the enamine (2; R2 = Me and Ph) with ethyl glycinate forms the ester (18) which on treatment with ethanolic sodium ethoxide produces the azepine (20).
About the journal
JournalData powered by TypesetJournal of the Chemical Society, Perkin Transactions 1
PublisherData powered by TypesetRoyal Society of Chemistry
ISSN1472-7781