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Convenient synthesis of 1,6,7,8-substituted 2-(3′,4′-substituted-phenyl)-4-quinolones via a 4-ethoxyflavylium salt

✍ Scribed by Shingo Sato; Takeshi Watanabe; Hironobu Kumagai; Nobuo Kitamura; Shigeru Matsuba; Toshihiro Kumazawa; Jun-Ichi Onodera; Masanobu Suzuki

Publisher
Journal of Heterocyclic Chemistry
Year
1999
Tongue
English
Weight
360 KB
Volume
36
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

Condensation of 2‐hydroxyacetophenone with benzaldehyde in the presence of 70% perchloric acid in ethyl orthoformate gave the corresponding 4‐ethoxyflavylium perchlorate, which was treated with aqueous ammonia or methylamine solution to afford 1,6,7,8‐substituted 2‐(3′,4′‐substituted‐phenyl)‐4‐quinolone in fair to good yield.

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Direct conversion to 2-phenyl-4-quinolon
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## Abstract A flavanone, in which a hydroxyl group at the 5‐position was protected with a methyl group, converted to the corresponding 5‐methoxy‐2‐phenyl‐4‐quinolone __via__ flavylium salt under mild conditions. Flavanone‐__O__‐rhamnoglucoside, naringin, was also converted to 5‐methoxy‐2‐phenyl‐4‐q