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Issue 10, 2012
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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

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Abstract

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.

Graphical abstract: 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

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Publication details

The article was received on 18 May 2012, accepted on 01 Aug 2012 and first published on 03 Aug 2012


Article type: Paper
DOI: 10.1039/C2GC35765H
Green Chem., 2012,14, 2876-2884

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    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

    A. Khalafi-Nezhad, S. Sarikhani, E. S. Shahidzadeh and F. Panahi, Green Chem., 2012, 14, 2876
    DOI: 10.1039/C2GC35765H

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