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Studies on heterocyclic compounds. VII. Syntheses of novel furo[2, 3‐ b ]chromones
Author(s) -
Kuo ShengChu,
Wu JiinSheng,
Huang LiJiau,
Wu ChunHsiung,
Huang ShunChueh,
Chou TehChang
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.5570260317
Subject(s) - chromone , chemistry , acylation , stereochemistry , furan , organic chemistry , medicinal chemistry , catalysis
Abstract Furo[2, 3‐ b ]chromone ( 1a ) was conveniently prepared by the PPE‐promoted cyclization of 5‐(2′‐carboxy‐phenoxy)furan‐2‐carboxylic acid ( 8 ) which was made from methyl salicylate and ethyl 5‐nitrofuran‐2‐carboxyl‐ate. Furo[2, 3‐ b ]chromon‐2‐acrylic acid ( 13 ) was obtained by a similar cyclization. Direct acylation of 1a afforded 2‐acetylfuro[2, 3‐ b ]chromone ( 10 ). Several derivatives of furo[2, 3‐ b ]chromone were found to display activity in the rat passive cutaneous anaphylaxis (PGA) test for antiallergic activity.