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Electrochemical reduction of N-(2-nitro-4-R-phenyl)pyridinium salts using redox-mediators

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Abstract

Electrochemical reduction of N-(2-nitroaryl)pyridinium chlorides was accomplished in acidic aqueous alcoholic medium in the galvanostatic mode using tin, titanium, vanadium, and iron chlorides as redox-mediators. The use of SnCl2 as a mediator catalyst made it possible to shorten the electrosynthesis time as compared to the direct electroreduction on an electrode and prepare the intramolecular cyclization products, viz., substituted pyrido[1,2-a]benzimidazoles, in high yield. The influence of the mediator nature and its amount, current density, temperature, cathode material, medium acidity, and the substrate structure on the efficiency of reductive heterocyclization of N-(2-nitroaryl)pyridinium salts was studied.

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Authors and Affiliations

  1. P. G. Demidov Yaroslavl State University, 14 ul. Sovetskaya, 150000, Yaroslavl, Russian Federation

    A. A. Sokolov & R. S. Begunov

  2. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    M. A. Syroeshkin, L. V. Mikhal’chenko, M. Yu. Leonova & V. P. Gul’tyai

Authors
  1. A. A. Sokolov
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  2. R. S. Begunov
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  3. M. A. Syroeshkin
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  4. L. V. Mikhal’chenko
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  5. M. Yu. Leonova
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  6. V. P. Gul’tyai
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Corresponding author

Correspondence to V. P. Gul’tyai.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 0209—0214, January, 2016.

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Sokolov, A.A., Begunov, R.S., Syroeshkin, M.A. et al. Electrochemical reduction of N-(2-nitro-4-R-phenyl)pyridinium salts using redox-mediators. Russ Chem Bull 65, 209–214 (2016). https://doi.org/10.1007/s11172-016-1286-2

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  • DOI: https://doi.org/10.1007/s11172-016-1286-2

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