喹啉酮类化合物合成与应用

Synthetic Communications Reviews

STUDIES ON QUINOLINEDIONE:SYNTHESIS,

REACTIONS,AND APPLICATIONS

Wafaa S.Hamama,Alaa El-Din E.Hassanien,and

HanafiH.Zoorob

Chemistry Department,Faculty of Science,Mansoura University,

Mansoura,Egypt

GRAPHICAL

ABSTRACT

Abstract In this account we present the rapidly expanding bibliography of published

research concerning the progress in the area of quioline-2,4-dione chemistry,including

synthetic strategies.

Keywords Quinolone;reaction application;synthesis

INTRODUCTION

Quinolone derivatives constitute an important class of nitrogen-containing heterocycles that have with diverse useful bioactivities.They are widely used as key intermediates in the preparation of some natural products and related structures.A broad number of fascinating pharmacological activities have been associated with 2-quinolinone derivatives.The quinolinone alkaloids isolated from the Rutaceae family of plants (Fig.1)have been shown to exhibit a variety of biological properties.The corresponding compounds exhibit similar properties,such as antibacterial,antifungal,and antivirial.[1,2]

On the basis of the biological evaluation,4-hydroxyquinolones constitute an important area of research because of their use as analgesics,dye stuffs,herbicides,orally active antagonists,and anti-inflammatory,antiallergenic,antitubercular,and cardiovascular agents.[3–6]

Received November 12,2013.

Address correspondence to Wafaa S.Hamama,Chemistry Department,Faculty of Science,Mansoura University,El-Gomhoria Street,ET-35516Mansoura,Egypt.E-mail:wshamama@

Synthetic Communications 1,44:1833–1858,2014

Copyright #Taylor &Francis Group,LLC

ISSN:0039-7911print =1532-2432online

DOI:

10.1080/00397911.2013.867352

1833

4-Hydroxyquinolines are important synthones and they are used as synthetic precursors of many naturally occurring alkaloids,polycyclic condensed heterocycles,multiazahetrocycles,isoxazolo quinolines,pyranoquinolines,piperazinyl carbomides,pyrazoloquinolines,and oxazinoquinolines.These derivatives are used as potent antiemetic,migraine-suppressing,antibacterial,fungicidal,antipyretic,anticoagulant,CNS,and memory enhancing agents and have shown anti-brain-tumor activity in vivo.[3]

SYNTHESIS OF QUINOLIN-2,4-DIONE DERIVATIVES

Reaction of Amine Derivatives with Acid Derivatives

4-Hydroxy-2(1H)quinolinone derivatives 1have been synthesized from the corresponding methyl N -(a -haloacyl)anthranilates (2)in the presence of sodium telluride [7](Scheme 1).

Biginelli reaction of the derivatives of 2-chlorobenzaldehyde,ethyl aceto-acetate,urea,or thiourea derivatives in the presence of boric acid afforded ethyl-4-phenyl-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates (3)or 4-phenyl-6-methyl-2-thia-1,2,3,4-tetrahydropyrimidine-5-carboxylates (4).These compounds undergo cyclization with ammonia under pressure to give 5and 6[8](Scheme

2).

Figure 1.Naturally occurring quinolone alkaloids.

1834W.S.HAMAMA,A.E.-D.E.HASSANIEN,AND H.H.ZOOROB