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Communication | Special issue | Vol 105, No. 1, 2022, pp.358-367
Published online, 20th May, 2022
DOI: 10.3987/COM-22-S(R)22
Synthesis of Benzo[d]pyrrolo[1,2-a]imidazoles by Iminocyclopropane Rearrangement of C-Cyclopropylbenzimidazoles

Adam P. Montoya, Matthew G. LaPorte, and Peter Wipf*

*Department of Chemistry, University of Pittsburgh, Pittsburgh PA 15260, USA


The MgI2 or NH4I mediated iminocyclopropane rearrangement of trisubstituted acrylonitrile benzimidazoles provides an attractive access to novel pyrrolo[1,2-a]imidazoles. The rearrangement precursors, C-cyclopropylbenzimidazoles, are obtained by a Corey-Chaykovsky cyclopropanation of the acrylonitrile. We determine the scope of the iminocyclopropane rearrangement to 2,3-dihydro-1H-benzo[d]pyrrolo[1,2-a]imidazole-3-carbonitrile and 2,4-dihydro-2,4-disubstituted as well as 1,2,4-trisubstituted 1H-benzo[d]pyrrolo[1,2-a]imidazole-3-carbonitriles, and describe some of the limitations and side reactions, including the formation of aromatized 4H-benzo[d]pyrrolo[1,2-a]imidazole-3-carbonitriles.