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Facile Synthesis of Novel Functionalized Pyridine Annulated Oxirane Methyl Coumarins
Author(s) -
Jayaprakash Rao Yerrabelly,
Dalal Shailendara,
Hemasri Yerrabelly,
Krupadanam G. L. David
Publication year - 2019
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.3460
Subject(s) - chemistry , pyridine , organic chemistry , coumarin
A one‐pot synthesis of series of new ethyl‐7‐oxirane methyl‐2‐methyl‐5‐oxo‐5 H ‐benzopyrano[3,4‐ c ]pyridine‐1‐carboxylates ( 6a–e ) from 3‐allyl‐2‐hydroxy acetophenones ( 1a–e ) via key intermediate 8‐allyl‐4‐chloro‐3‐formyl coumarins ( 2a–e ) is described. The reaction involves Michael addition of 8‐allyl‐4‐chloro‐3‐formyl coumarins with ethyl 3‐amino crotonoate followed by cyclization, and per acid epoxidation proceeds under mild conditions and gives products in good‐to‐excellent yields.