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1,5-Electrocyclization of 1-alkyl- 3-[(2Z)-2,4-diaryl-4-oxobut-2-en-1-yl]-1H-benzimidazol-3-ium bromides

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Chemistry of Heterocyclic Compounds Aims and scope

Cyclization of 1-alkyl-3-[(2Z)-2,4-diaryl-4-oxobut-2-en-1-yl]-1H-benzimidazol-3-ium bromides occurs in the presence of MeONa at a reduced temperature of 5–10°C via a 1,5-electrocyclization mechanism to give 3a,4-dihydro-3H-pyrrolo[1,2-a]benzimidazoles. These are unstable under the reaction conditions and are readily converted to {1-[2-(alkylamino)phenyl]-4-phenyl-1H-pyrrol-3-yl}(phenyl)methanones.

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Correspondence to L. M. Potikha.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 552–556, April, 2011.

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Potikha, L.M., Turelyk, A.R. & Kovtunenko, V.A. 1,5-Electrocyclization of 1-alkyl- 3-[(2Z)-2,4-diaryl-4-oxobut-2-en-1-yl]-1H-benzimidazol-3-ium bromides. Chem Heterocycl Comp 47, 452–455 (2011).

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