Synthesis of 4‐hydroxyquinolin‐2(1 H )‐one analogues and 2‐substituted quinolone derivatives
2001; Wiley; Volume: 38; Issue: 1 Linguagem: Inglês
10.1002/jhet.5570380109
ISSN1943-5193
AutoresJae‐Chul Jung, Young‐Jo Jung, Oee‐Sook Park,
Tópico(s)Synthesis of heterocyclic compounds
ResumoAbstract 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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