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A New Four-Component Reaction Involving Michael Addition and Gewald Reaction, Leading to Diverse Biologically Active 2-Aminothiophenes

Abstract

The Gewald three-component reaction yielding highly substituted 2-aminothiophene heterocycles has been known for a long time and holds an extraordinary potential in pharmaceutical industry. Herein, we describe a four-component reaction initiated by the conjugate addition of different indole derivatives to α, β-unsaturated carbonyl compounds. This is followed by an in situ Gewald three-component reaction which results in the formation of a compound containing an indole and a 2-aminothiophene moiety separated by a methylene spacer. We also examined the impact of the use of other nucleophilic components such as pyrrole derivatives on this MG-4CR (Michael-Gewald four component reaction). All these synthesized compounds were tested for anti-proliferative activity and three of them showed activity in the nanomolar range.

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Publication details

The article was accepted on 09 Apr 2017 and first published on 11 Apr 2017


Article type: Paper
DOI: 10.1039/C7OB00707H
Citation: Org. Biomol. Chem., 2017, Accepted Manuscript
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    A New Four-Component Reaction Involving Michael Addition and Gewald Reaction, Leading to Diverse Biologically Active 2-Aminothiophenes

    J. Thomas, S. Jana, M. Sonawane, B. Fiey, J. Balzarini, S. Liekens and W. Dehaen, Org. Biomol. Chem., 2017, Accepted Manuscript , DOI: 10.1039/C7OB00707H

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