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Issue 6, 2015
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A multicomponent pathway-inspired regioselective synthesis of 2,3,4-trisubstituted 1H-pyrroles via [3+2] cycloaddition reaction

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Abstract

A copper catalyzed regioselective synthesis of 2,3,4-trisubstituted 1H-pyrroles using a novel three-component coupled domino reaction of aldehydes, ketones and alkyl isocyanoacetates is reported. This transformation proceeds through the formation of a chalcone followed by a [3+2] cycloaddition reaction to obtain α-cuprioisocyanide, a cyclic organocopper intermediate, which on copper–hydrogen exchange followed by oxidation exclusively offers 2,3,4-trisubstituted 1H-pyrrole.

Graphical abstract: A multicomponent pathway-inspired regioselective synthesis of 2,3,4-trisubstituted 1H-pyrroles via [3+2] cycloaddition reaction

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Article information


Submitted
03 Feb 2015
Accepted
30 Mar 2015
First published
16 Apr 2015

New J. Chem., 2015,39, 4631-4639
Article type
Paper
Author version available

A multicomponent pathway-inspired regioselective synthesis of 2,3,4-trisubstituted 1H-pyrroles via [3+2] cycloaddition reaction

H. P. Kalmode, K. S. Vadagaonkar, K. Murugan and A. C. Chaskar, New J. Chem., 2015, 39, 4631
DOI: 10.1039/C5NJ00302D

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