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Mechanism and products of electrochemical reduction of 4-nitrophenyl-2,6-dimethyl-3,5-dicyano-1,4-dihydropyridines in dimethylformamide

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Free anion radicals of the nitrobenzene and nitrosobenzene type, which were identified by EPR spectroscopy, are formed in the electrochemical reduction of isomeric 4-(nitrophenyl)-2,6-dimethyl-3,5-dicyano-1,4-dihydropyridines on mercury and solid electrodes. Reduction of the dihydropyridine ring is observed only for N-substituted p- and m-nitrophenyl derivatives of 1,4-dihydropyridine. An intermediate with a 2-pyridonemethide structure was identified; a set of primary and secondary chemical reactions that are associated with the electrolytic reduction of the investigated compounds is presented.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1494–1505, November, 1988.

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Baumane, L.K., Stradyn', Y.P., Gavar, R.A. et al. Mechanism and products of electrochemical reduction of 4-nitrophenyl-2,6-dimethyl-3,5-dicyano-1,4-dihydropyridines in dimethylformamide. Chem Heterocycl Compd 24, 1238–1248 (1988). https://doi.org/10.1007/BF00633503

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  • DOI: https://doi.org/10.1007/BF00633503

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