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The first examples of Nazarov cyclizations leading to annulated pyrroles.

[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.[1]


  1. The first examples of Nazarov cyclizations leading to annulated pyrroles. Song, C., Knight, D.W., Whatton, M.A. Org. Lett. (2006) [Pubmed]
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