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Org Lett. 2006 Jan 5;8(1):163-6.

The first examples of Nazarov cyclizations leading to annulated pyrroles.

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  • 1School of Chemistry, Cardiff University, Main College, UK.

Abstract

[reaction: see text] Reactions between alpha-substituted unsaturated carboxylic acids 20 and N-tosylpyrroles [14, 23] in the presence of trifluoroacetic anhydride result in smooth alpha-acylation of the pyrrole, followed by Nazarov cyclization to give 50-80% yields of cyclopenta[b]pyrroles. The presence of an alpha-substituent in the unsaturated acid appears to be mandatory.

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