Open Access Open Access  Restricted Access Subscription Access

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

Л. В. Андриянкова, Л. П. Никитина, К. В. Беляева, А. Г. Малькина, А. В. Афонин, А. В. Ващенко, В. И. Смирнов, Б. А. Трофимов
Cover Image

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


Keywords


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

Full Text: PDF (Russian) Supplementary File(s): None


 

 

Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv