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Synthesis of 4-hydroxyquinolin-2(1H)-one analogues and 2-substituted quinolone derivatives

✍ Scribed by Jae-Chul Jung; Young-Jo Jung; Oee-Sook Park

Publisher
Journal of Heterocyclic Chemistry
Year
2001
Tongue
English
Weight
83 KB
Volume
38
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

A versatile synthetic method for preparing 4‐hydroxyquinolone and 2‐substituted quinolone compounds from simple benzoic acid derivatives was demonstrated. The synthetic strategies involve the use of well known ethyl acetoacetate synthesis, malonic ester synthesis and reductive cyclization. The key intermediates were keto esters 4a‐e, which could be transformed to 4‐hydroxyquinolones 5a,b or 2‐substituted quinolone ethyl esters 6a‐c depending on the reaction conditions. 4‐Hydroxyquinolone analogues were prepared and investigated for N‐methyl‐D‐aspartate (NMDA) activity in vitro. Among these derivatives, 6,7‐difluoro‐3‐nitro‐4‐hydroxyquinolin‐2(1__H__)‐one (9) exhibited moderate activity.

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