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J Org Chem. 2013 Dec 6;78(23):11860-73. doi: 10.1021/jo401892t. Epub 2013 Nov 26.

A general route to 1,3'-bipyrroles.

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  • 1Chemistry Department, University of Alberta , Edmonton, Alberta T6G 2G2, Canada.

Abstract

A general method is described for the synthesis of 1,3'-bipyrroles. The route involves constructing a pyrrole ring on the nitrogen of a substituted 1H-pyrrole, so as to generate the 1,3'-bipyrrole. In this approach the nitrogen of the starting pyrrole was alkylated with a special Michael acceptor having an allylic leaving group, and the product was then modified in such a way that the second pyrrole ring could be formed by a Paal-Knorr reaction. Two variants of this sequence were examined, one of which led to formation of a 3-hydroxypyridine instead of the second pyrrole ring; the other variant used phenacyl bromide instead of the special Michael acceptor.

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