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Synthesis of 4‐hydroxyquinolin‐2(1 H )‐one analogues and 2‐substituted quinolone derivatives
Author(s) -
Jung JaeChul,
Jung YoungJo,
Park OeeSook
Publication year - 2001
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.5570380109
Subject(s) - chemistry , quinolone , ethyl acetoacetate , benzoic acid , nitro , combinatorial chemistry , stereochemistry , organic chemistry , antibiotics , catalysis , biochemistry , alkyl
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.