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Stereoselective Synthesis of N-[(Z)-2-Cyano-1-Phenylethenyl]Benzimidazole-2-Carbothioamides by a Three-Component Reaction of 1-Substituted Benzimidazoles, Phenylcyanoacetylene, and Isothiocyanates

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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This work was carried out with the financial support of the Program of the Department of Chemistry and Material Sciences of the Russian Academy of Sciences (grant No. 5.1.3.) and the Grants Council of the President of the Russian Federation (grant NSh 156.2014.3). The major results were obtained using the material and technical structure of the Baikal Analytical Center of Collective Using of the Siberian Branch of the Russian Academy of Sciences.

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Authors and Affiliations

  1. A. E. Favorsky Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky St., Irkutsk, 664033, Russia

    L. V. Andriyankova, L. P. Nikitina, K. V. Belyaeva, A. G. Mal’kina, A. V. Afonin, A. V. Vashchenko, V. I. Smirnov & B. A. Trofimov

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  1. L. V. Andriyankova
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  2. L. P. Nikitina
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  3. K. V. Belyaeva
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  4. A. G. Mal’kina
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  5. A. V. Afonin
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  6. A. V. Vashchenko
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  7. V. I. Smirnov
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  8. B. A. Trofimov
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Corresponding author

Correspondence to B. A. Trofimov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 876-882, June, 2014.

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Andriyankova, L.V., Nikitina, L.P., Belyaeva, K.V. et al. Stereoselective Synthesis of N-[(Z)-2-Cyano-1-Phenylethenyl]Benzimidazole-2-Carbothioamides by a Three-Component Reaction of 1-Substituted Benzimidazoles, Phenylcyanoacetylene, and Isothiocyanates. Chem Heterocycl Comp 50, 807–813 (2014). https://doi.org/10.1007/s10593-014-1535-y

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  • DOI: https://doi.org/10.1007/s10593-014-1535-y

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