☆ 4.7 Article

Domino Knoevenagel condensation, Michael addition, and cyclization using ionic liquid, 2-hydroxyethylammonium formate, as a recoverable catalyst

JOURNAL OF MOLECULAR LIQUIDS (2011)

Journal

JOURNAL OF MOLECULAR LIQUIDS

Volume 158, Issue 2, Pages 145-150

Publisher

ELSEVIER

DOI: 10.1016/j.molliq.2010.11.010

Keywords

Benzylidenemalononitriles; 2-Benzylidene-5,5-dimethylcyclohexane-1,3-diones; 2-Amino-5-oxo-4-aryl-4,5-dihydropyrano[3,2-c]chromene-3-carbonitrile; Tetrahydrobenzo[b]pyran; Ionic liquid; Spirooxindole

Categories

Chemistry, Physical Physics, Atomic, Molecular & Chemical

Funding

University of Sistan
Baluchestan Research Council

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Abstract

The Knoevenagel condensation reaction of aromatic aldehydes with malononitrile or dimedone was investigated. Also, the three-component and one-pot synthesis of 2-amino-5-oxo-4-aryl-4,5-dihydropyrano [3,2-c]chromene-3-carbonitrile derivatives by condensing 4-hydroxycoumarin, aldehydes and malononitriles using a catalytic amount of 2-hydroxyethylammonium formate as an effective ionic liquid without using any additional co-catalyst under solvent-free conditions at room temperature is reported. Furthermore, the domino Knoevenagel condensation, conjugate addition, and cyclization for the preparation of tetrahydrobenzo[b]pyran, and spirooxindole derivatives in high atomic efficiency take place in excellent yields. (C) 2010 Elsevier B.V. All rights reserved.

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