1,5-ELECTROCYCLIZATION OF 1-ALKYL-3-[(2<i>Z</i>)-2,4-DIARYL-4-OXOBUT-2-EN-1-YL]-1<i>H</i>-BENZIMIDAZOL-3-IUM BROMIDES

Authors

  • Л. М. Потиха Taras Shevchenko National University
  • А. Р. Турелик Taras Shevchenko National University
  • В. А. Ковтуненко Taras Shevchenko National University

DOI:

https://doi.org/10.1007/2072

Keywords:

benzimidazolium ylide, pyrido[1, 2-a]benzimidazole, pyrrolo[1, 1, 5-electrocyclization

Abstract

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 5–10ºC 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.

How to Cite
Potikha, L. M.; Turelyk, A. R.; Kovtunenko, V. A. Chem. Heterocycl. Compd. 2011, 47(4), 452. [Khim. Geterotsikl. Soedin. 2011, 552.]

For this article in the English edition see DOI 10.1007/s10593-011-0780-6

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Published

2014-11-27

Issue

No. 4 (2011)

Section

Original Papers