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Electrochemical Oxidative Aromatizationof 9-Substituted 9,10-Dihydroacridines: Cleavage of C–H vs C–X Bond

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Chemistry of Heterocyclic Compounds Aims and scope

Reactivity of dihydroacridines bearing a С–X fragment at the geminal C-9 atom (where X = C, N, O, P, S) on anode has been investigated by means of electrochemical oxidation and thermodynamic and quantum-chemical calculations. The electrochemical oxidation results either in the formation of the 9-substituted acridines or in the cleavage of the C–X bond. This dual behavior of dihydroazines is analogous to processes reported in literature that take place upon treatment with chemical oxidants.

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ACKNOWLEDGMENT

The research was financially supported by the Russian Foundation for Basic Research (research project No. 18-33-00124).

Analytical studies were carried out using equipment of the Center for Joint Use “Spectroscopy and Analysis of Organic Compounds” at the Postovsky Institute of Organic Synthesis of the Russian Academy of Sciences (Ural Branch).

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Authors and Affiliations

  1. Postovsky Institute of Organic Synthesis, Russian Academy of Sciences, 20 Akademicheskaya / 22 S. Kovalevskoi St., Yekaterinburg, 620990, Russia

    Oleg N. Chupakhin, Alexander V. Shchepochkin, Valery N. Charushin & Pavel A. Slepukhin

  2. Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg, 620002, Russia

    Oleg N. Chupakhin, Alexander V. Shchepochkin, Valery N. Charushin, Anna V. Maiorova, Tatyana V. Kulikova, Konstantin Yu. Shunyaev, Pavel A. Slepukhin & Anna I. Suvorova

  3. Institute of Metallurgy, Ural Branch of the Russian Academy of Sciences, 101 Amundsena St., Yekaterinburg, 620016, Russia

    Anna V. Maiorova, Tatyana V. Kulikova & Konstantin Yu. Shunyaev

  4. Institute of Solid State Chemistry, Ural Branch of the Russian Academy of Sciences, 91 Pervomaiskaya St., Yekaterinburg, 620990, Russia

    Andrey N. Enyashin

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  1. Oleg N. Chupakhin
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  2. Alexander V. Shchepochkin
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Correspondence to Oleg N. Chupakhin.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(10), 956–963

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Chupakhin, O.N., Shchepochkin, A.V., Charushin, V.N. et al. Electrochemical Oxidative Aromatizationof 9-Substituted 9,10-Dihydroacridines: Cleavage of C–H vs C–X Bond. Chem Heterocycl Comp 55, 956–963 (2019). https://doi.org/10.1007/s10593-019-02562-x

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