Issue 9, 2015
From the journal:

Organic & Biomolecular Chemistry

Expedient synthesis of tetrasubstituted pyrroles via a copper-catalyzed cascade inter-/intramolecular cyclization of 1,3-enynes carry a nitro group with amines†

Ganesan Bharathiraja,a   Mani Sengoden,a   Masanam Kannana  and  Tharmalingam Punniyamurthy*a  

* Corresponding authors

a Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, India
E-mail: tpunni@iitg.ernet.in

Abstract

Various tetrasubstituted pyrroles/pyrazoles have been prepared from nitro-substituted 1,3-enynes with aromatic amines/hydrazines via a copper-catalyzed cascade aza-Michael addition, cyclization and aromatization at room temperature. This protocol is also effective for the synthesis of tetrasubstituted pyrazoles in high yields.

Graphical abstract: Expedient synthesis of tetrasubstituted pyrroles via a copper-catalyzed cascade inter-/intramolecular cyclization of 1,3-enynes carry a nitro group with amines

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Article information

DOI
https://doi.org/10.1039/C4OB02508C
Article type
Paper
Submitted
29 Nov 2014
Accepted
09 Jan 2015
First published
12 Jan 2015

Org. Biomol. Chem., 2015,13, 2786-2792

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Expedient synthesis of tetrasubstituted pyrroles via a copper-catalyzed cascade inter-/intramolecular cyclization of 1,3-enynes carry a nitro group with amines

G. Bharathiraja, M. Sengoden, M. Kannan and T. Punniyamurthy, Org. Biomol. Chem., 2015, 13, 2786 DOI: 10.1039/C4OB02508C

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