L-Proline-promoted three-component reaction of anilines, aldehydes and barbituric acids/malononitrile: regioselective synthesis of 5-arylpyrimido-[4,5-b] quinoline-diones and 2-amino-4-arylquinoline-3-carbonitriles in water

被引：98
作者：
Khalafi-Nezhad, Ali [1 ]
Sarikhani, Samira [1 ]
Shahidzadeh, Elham Shaikhi [1 ]
Panahi, Farhad [1 ]
机构：
[1] Shiraz Univ, Coll Sci, Dept Chem, Shiraz 71454, Iran
来源：
GREEN CHEMISTRY | 2012年 / 14卷 / 10期
关键词：
ONE-POT SYNTHESIS; ASYMMETRIC ALDOL REACTIONS; EFFICIENT ONE-POT; MULTICOMPONENT REACTIONS; BIFUNCTIONAL ORGANOCATALYST; MULTIDRUG-RESISTANCE; ANTITUMOR-ACTIVITY; CYCLIC ANHYDRIDES; MICHAEL ADDITION; BAYLIS-HILLMAN;
D O I：
10.1039/c2gc35765h
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A green and efficient one-pot process to achieve 5-aryl-pyrimido[4,5-b] quinoline-dione derivatives, using a three-component reaction involving anilines, aldehydes and barbituric acids was developed. This protocol was accomplished efficiently using L-proline as catalyst in an aqueous medium to give the corresponding products in high yield. Also, 2-amino-4-arylquinoline-3-carbonitrile derivatives were obtained by replacing the barbituric acid with malononitrile in the designed protocol. The catalytic activity of L-proline in these reactions was tested over a set of aldehydes and amines, demonstrating that it is reactive towards a variety of functionalities. The multicomponent reactions showed good regioselectivity, and computational studies were used to investigate the selectivity.
引用
收藏
页码：2876 / 2884
页数：9
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