Issue 8, 2014

Imidazole as organocatalyst for multicomponent reactions: diversity oriented synthesis of functionalized hetero- and carbocycles using in situ-generated benzylidenemalononitrile derivatives

Abstract

The multicomponent reaction of malononitrile, aldehyde and a third reaction partner such as naphthol/4-hydroxycoumarine/2-hydroxynaphthoquinone/kojic acid/enolizable ketone or thiol in the presence of imidazole as an organocatalyst provides very interesting molecular diversity. In an almost neutral reaction medium, this protocol provides easy access to highly functionalized 2-amino-4H-chromenes, dienes and 2-amino pyridines using in situ-generated aryl/alkylylidenemalononitrile derivatives obtained from the reaction of aldehydes and malononitrile along with various nucleophiles under reflux conditions in ethanol. This methodology is useful for the easy access of a wide range of structurally diverse functionalized molecules having potential application in biological systems.

Graphical abstract: Imidazole as organocatalyst for multicomponent reactions: diversity oriented synthesis of functionalized hetero- and carbocycles using in situ-generated benzylidenemalononitrile derivatives

Supplementary files

Article information

Article type
Paper
Submitted
20 sept. 2013
Accepted
23 oct. 2013
First published
24 oct. 2013

RSC Adv., 2014,4, 3732-3741

Imidazole as organocatalyst for multicomponent reactions: diversity oriented synthesis of functionalized hetero- and carbocycles using in situ-generated benzylidenemalononitrile derivatives

Md. N. Khan, S. Pal, S. Karamthulla and L. H. Choudhury, RSC Adv., 2014, 4, 3732 DOI: 10.1039/C3RA45252B

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