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Unusual Reduction of Benzofuroxans to Benzofurazans with the Participation of the Terminal Amino Group

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Abstract

The possibility of spontaneous reduction of benzofuroxans to benzofurazans in course of time due to reactions with diamines was shown for the first time. A possible mechanism of the reaction of 4,6-dichloro-5-nitrobenzofuroxan with diamines and related amines was analyzed by the quantum-chemical method. The results of research fully confirm the obtained experimental data and explain the impossibility of the subsequent reduction of amino-containing benzofuroxans due to a high activation barrier.

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Funding

The synthetic part of the work was carried out with the financial support of the Russian Science Foundation and the Cabinet of Ministers of the Tatarstan Republic within the framework of scientific project No. 22-23-20015, https://rscf.ru/project/22-23-20015/. Quantum chemical calculations were carried out with financial support from the state assignment of the Federal Kazan Scientific Center of the Russian Academy of Sciences. Physicochemical studies were carried out on the equipment of the Collective Spectro-Analytical Center for the Study of the Structure, Properties and Composition of Substances And Materials of the Federal Kazan Scientific Center of the Russian Academy of Sciences.

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Authors and Affiliations

  1. L.N. Gumilyov Eurasian National University, 010008, Astana, Kazakhstan

    M. N. Zhanakov & Zh. K. Zhatkanbayeva

  2. Arbuzov Institute of Organic and Physical Chemistry, Kazan Research Center, Russian Academy of Sciences, 420088, Kazan, Russia

    V. I. Matveeva, E. A. Chugunova, A. R. Khamatgalimov, A. R. Burilov & A. B. Dobrynin

  3. Korkyt Ata Kyzylorda University, 120014, Kyzylorda, Kazakhstan

    N. I. Akylbekov

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  1. M. N. Zhanakov
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Correspondence to N. I. Akylbekov.

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A.R. Burilov is a member of the editorial board of the Journal of General Chemistry. The remaining authors declare no conflict of interest.

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Zhanakov, M.N., Matveeva, V.I., Akylbekov, N.I. et al. Unusual Reduction of Benzofuroxans to Benzofurazans with the Participation of the Terminal Amino Group. Russ J Gen Chem 93 (Suppl 2), S491–S500 (2023). https://doi.org/10.1134/S1070363223150112

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