SIGNS OF FORMATION AND CHEMICAL EVOLUTION OF ZWITTERIONS IN THE REACTION OF 1-METHYLIMIDAZOLE WITH CYANOPHENYLACETYLENE AND BENZALDEHYDE

Authors

  • Л. В. Андриянкова A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences
  • К. В. Беляева A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences
  • Л. П. Никитина A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences
  • А. Г. Малькина A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences
  • Т. И. Вакульская A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences
  • С. С. Хуцишвили A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences
  • Л. М. Синеговская A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences
  • Б. А. Трофимов A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences

DOI:

https://doi.org/10.1007/1349

Keywords:

aldehydes, carbenes, cyanoacetylenes, 1-substituted imidazoles, zwitterions, monitoring reaction, multicomponent reactions, nucleophilic addition

Abstract

Primary monitoring of the three-component reaction of 1-methylimidazole with cyanophenylacetylene and benzaldehyde by EPR, UV, NMR, and IR spectroscopy has been carried out. Experimental evidence has been obtained for the formation of zwitterions and carbenes of the imidazole series as intermediates of a new functionalization reaction of the imidazole ring leading to 2-benzoyl-3-(1-methyl-1H-imidazol-2-yl)-3-phenylpropanenitrile.

Authors: L. V. Andriyankova, K. V. Belyaeva, L. P. Nikitina, A. G. Mal'kina, T. I. Vakul'skaya, S. S. Khutsishvili, L. M. Sinegovskaya, and B. A. Trofimov.

English translation in Chemistry of Heterocyclic Compounds, 2011, 47 (11), pp 1390-1394

http://link.springer.com/article/10.1007/s10593-012-0926-1

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Published

2013-12-12

Issue

No. 11 (2011)

Section

Original Papers