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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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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DOI: https://doi.org/10.1007/s10593-019-02562-x