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Alkylation and Aminomethylation of 1,3-Dihydro-2Н-Benzimidazole-2-Thione

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Chemistry of Heterocyclic Compounds Aims and scope

Alkylation of 1,3-dihydro-2Н-benzimidazole-2-thione (2-mercaptobenzimidazole) with bromoethane and chloroacetic acid derivatives occurrs at the sulfur atom, leading to the corresponding 2-sulfanylbenz-imidazole derivatives. Aminomethylation of 1,3-dihydro-2Н-benzimidazole-2-thione with piperidine and 4-methylpiperidine gives reaction products at both nitrogen atoms, while reaction with morpholine gives derivative at only one nitrogen atom, which is in an equilibrium with the starting compound and bis-adduct in DMSO solution.

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This work received financial support from the Russian Science Foundation (grant No. 14-13-00126). The experiments were performed by using equipment at the Saint Petersburg State University Resource Centers "Center for Magnetic Resonance Research", "Center for X-ray Diffraction Studies", "Center for Chemical Analysis and Material Research".

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Authors and Affiliations

  1. Institute of Toxicology, Federal Medical-Biological Agency of the Russian Federation, 1 Bekhtereva St, Saint Petersburg, 192019, Russia

    A. Ya. Bespalov, T. L. Gorchakova & L. I. Prokopenko

  2. Saint Petersburg State University, 26 Universitetsky Ave., Saint Petersburg, 198504, Russia

    A. Yu. Ivanov, M. A. Kuznetsov, L. M. Kuznetsova & A. S. Pankova

  3. Research Center for X-ray Diffraction Studies, Saint Petersburg State University, 26 Universitetsky Ave., Saint Petersburg, 198504, Russia

    M. S. Avdontceva

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  1. A. Ya. Bespalov
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  2. T. L. Gorchakova
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  3. A. Yu. Ivanov
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  4. M. A. Kuznetsov
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  5. L. M. Kuznetsova
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Correspondence to M. A. Kuznetsov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1684–1696, November, 2014.

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Bespalov, A.Y., Gorchakova, T.L., Ivanov, A.Y. et al. Alkylation and Aminomethylation of 1,3-Dihydro-2Н-Benzimidazole-2-Thione. Chem Heterocycl Comp 50, 1547–1558 (2015). https://doi.org/10.1007/s10593-014-1623-z

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