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Synthesis of heterocycles on the basis of 1,5-diketone hydrazones. 2. Oxidative cyclization of δ-bicyclanone bis(phenylhydrazones) as a method for the synthesis of substituted 2-phenyl-4R-Δ1(sa)-octahydrocinnoline-3-spirocy clohexanes

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Abstract

The oxidation of δ-bicyclanone bis (phenylhydrazones) with oxygen or ferric chloride leads to the formation of 2-phenyl-4R-Δ1(sa)-octahydrocinnoline-3-spiro-1′-cyclohexan-2′-one phenylhydrazones. The structures of these compounds were proved by the 13C NMR, IR, and mass spectra, as well as by transformations in acidic media to the corresponding keto derivatives and tetrahydrocarbazole derivatives.

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Authors and Affiliations

  1. Far Eastern State University, 690600, Vladivostok

    T. V. Moskovkina & M. N. Tilichenko

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  1. T. V. Moskovkina
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  2. M. N. Tilichenko
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See [1] for Communication 1.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 821–825, June, 1983.

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Moskovkina, T.V., Tilichenko, M.N. Synthesis of heterocycles on the basis of 1,5-diketone hydrazones. 2. Oxidative cyclization of δ-bicyclanone bis(phenylhydrazones) as a method for the synthesis of substituted 2-phenyl-4R-Δ1(sa)-octahydrocinnoline-3-spirocy clohexanes. Chem Heterocycl Compd 19, 661–665 (1983). https://doi.org/10.1007/BF00523082

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  • DOI: https://doi.org/10.1007/BF00523082

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