STEREOSELECTIVE SYNTHESIS OF <i>N</i>-[(<i>Z</i>)-2-CYANO-1-PHENYLETHENYL]BENZIMIDAZOLE-2-CARBOTHIOAMIDES BY A THREE-COMPONENT REACTION OF 1-SUBSTITUTED BENZIMIDAZOLES, PHENYLCYANOACETYLENE, AND ISOTHIOCYANATES

Authors

  • Л. В. Андриянкова A. E. Favorsky Institute of Chemistry, Siberian Branch, Russian Academy of Sciences
  • Л. П. Никитина A. E. Favorsky Institute of Chemistry, Siberian Branch, Russian Academy of Sciences
  • К. В. Беляева A. E. Favorsky Institute of Chemistry, Siberian Branch, Russian Academy of Sciences
  • А. Г. Малькина A. E. Favorsky Institute of Chemistry, Siberian Branch, Russian Academy of Sciences
  • А. В. Афонин A. E. Favorsky Institute of Chemistry, Siberian Branch, Russian Academy of Sciences
  • А. В. Ващенко A. E. Favorsky Institute of Chemistry, Siberian Branch, Russian Academy of Sciences
  • В. И. Смирнов A. E. Favorsky Institute of Chemistry, Siberian Branch, Russian Academy of Sciences
  • Б. А. Трофимов A. E. Favorsky Institute of Chemistry, Siberian Branch, Russian Academy of Sciences

DOI:

https://doi.org/10.1007/1775

Keywords:

benzimidazoles, carbenes, isothiocyanates, phenylcyanoacetylene, nucleophilic addition, three-component reactions, zwitterions

Abstract

A new method has been developed for the synthesis of benzimidazole carbothioamides, which have potential pharmacological activity, by a three-component reaction of 1-substituted benzimidazoles, phenylcyanoacetylene, and methyl, allyl, or phenyl isothiocyanates. The reaction of these components proceeds under mild conditions in acetonitrile at 50-55°C for 12-20 h and stereoselectively leads to N‑[(Z)-2-cyano-1-phenylethenyl]benzimidazole-2-carbothioamides in 43-82% yield.

How to Cite
Andriyankova, L. V.; Nikitina, L. P.; Belyaeva, K. V.; Mal'kina, A. G.; Afonin, A. V.; Vashchenko, A. V.; Smirnov, V. I.; Trofimov, B. A. Chem. Heterocycl. Compd. 2014, 50, 807. [Khim. Geterotsikl. Soedin. 2014, 876.]

For this article in the English edition see DOI 10.1007/s10593-014-1535-y

Author Biography

Б. А. Трофимов, A. E. Favorsky Institute of Chemistry, Siberian Branch, Russian Academy of Sciences

Борис Александрович Трофимов

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Published

2014-06-26

Issue

No. 6 (2014)

Section

Original Papers