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Synthesis of new 2 H ,4 H ‐benzopyrano[3,4‐ b ]yridine‐1,3,5‐trione derivatives via carbon suboxide
Author(s) -
Bonsignore Leonardo,
Loy Giuseppe
Publication year - 1998
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.5570350122
Subject(s) - chemistry , pyridine , hydrolysis , coumarin , medicinal chemistry , hydrogen chloride , chloride , carbon fibers , lewis acids and bases , organic chemistry , catalysis , materials science , composite number , composite material
The new 2 H ,4 H ‐[1]benzopyrano[3,4‐ b ]pyridine‐1,3,5‐trione derivatives 10a‐f were prepared in the following three steps: first the preparation of new N ‐( tert ‐butoxycarbonyl)‐3‐amino‐2 H ‐1‐benzopyran‐2‐one derivatives 5a‐f by reaction of coumarin‐3‐carboxylic acids and diphenylphosphorylazide, then hydrolysis of 5a‐f with gaseous hydrogen chloride to give the corresponding amines 7a‐f , and finally the preparation of 10a‐f by reaction of 7a‐f and carbon suboxide in the presence of a Lewis acid.