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Reductive acid-catalyzed rearrangement of 3-(2-nitrobenzyl)quinoxalin-2(1Н)-ones in the presence of Na2S2O4 – effective method for the synthesis of 2-(indol-2-yl)benzimidazoles

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Chemistry of Heterocyclic Compounds Aims and scope

An effective one-step method is proposed for the synthesis of 2-(indol-2-yl)benzimidazoles from 3-(2-nitrobenzyl)quinoxalin-2(1Н)-ones without using metal catalysts and reagents. This method is based on the Mamedov rearrangement of 3-(2-aminobenzyl)quinoxalin-2(1Н)-ones, formed in situ by the action of Na2S2O4, giving 2-(indol-2-yl)benzimidazoles as the products.

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The work was supported in part by the Russian Science Foundation (project No. 14-23-00073-p).

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  1. A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center of the Russian Academy of Sciences, 8 Akademika Arbuzova St., Kazan, 420088, Tatarstan, Russia

    Vakhid A. Mamedov, Elena A. Khafizova, Victor V. Syakaev, Olga B. Bazanova, Anastasiya I. Zamaletdinova, Il’dar Kh. Rizvanov, Shamil K. Latypov & Oleg G. Sinyashin

  2. Kazan National Research Technological University, 68 Karla Marksa St., Kazan, 420015, Tatarstan, Russia

    Vakhid A. Mamedov, Elena A. Khafizova, Anastasiya I. Zamaletdinova & Oleg G. Sinyashin

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(9), 1033–1044

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Mamedov, V.A., Khafizova, E.A., Syakaev, V.V. et al. Reductive acid-catalyzed rearrangement of 3-(2-nitrobenzyl)quinoxalin-2(1Н)-ones in the presence of Na2S2O4 – effective method for the synthesis of 2-(indol-2-yl)benzimidazoles. Chem Heterocycl Comp 53, 1033–1044 (2017). https://doi.org/10.1007/s10593-017-2166-x

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