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Oxidative coupling of 4a,9-diaza-1,2,4a,9a-tetrahydrofluorenes. 1. Synthesis of mononuclear heterocyclic quinonediimines

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Abstract

Oxidative coupling of 4a,9-diaza-1,2,4a,9a-tetrahydro-9H-fluorene with primary amines and ammonia in the presence of MnO2 gives the corresponding 6-aryl (or alkyl)imino-4a,9-diaza-1,2,4a,9a-tetrahydro-6H-fluorenes. Coupling with thiourea under these conditions affords 6-cyanoimino-4a,9-diaza-1,2,4a,9a-tetrahydro-6H-fluorenes.

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Literature Cited

  1. V. A. Kaminskii, O. Yu. Slabko, and M. N. Tilicheko, Khim. Geterotsikl. Soedin., No. 6, 793 (1988).

    Google Scholar 

  2. N. N. Vorozhtsov, Fundamentals of the Synthesis of Intermediates and Dyes [in Russian], Goskhimizdat, Moscow (1955).

    Google Scholar 

  3. R. K. Heines and F. R. Hewgill, J. Chem. Soc., Perkin 1, No. 6, 813 (1972).

    Google Scholar 

  4. M. Hedajatullah, J. Deshatre, and L. Denivelle, Tetrahedron Lett., No. 25, 2039 (1975).

    Google Scholar 

  5. A. Aumüller and S. Hünig, Liebigs, Ann. Chem., No. 1, 165 (1986).

    Google Scholar 

  6. V. A. Kaminskii, O. Yu. Slabko, S. é. Kraeva, and M. N. Tilichenko, Zh. Org. Khim., 24, 228 (1988).

    Google Scholar 

  7. A. I. Fatiadi, Synthesis, No. 2, 76 (1976).

    Google Scholar 

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1500–1504, November, 1989.

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Slabko, O.Y., Kaminskii, V.A. & Tilichenko, M.N. Oxidative coupling of 4a,9-diaza-1,2,4a,9a-tetrahydrofluorenes. 1. Synthesis of mononuclear heterocyclic quinonediimines. Chem Heterocycl Compd 25, 1254–1258 (1989). https://doi.org/10.1007/BF00481519

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  • DOI: https://doi.org/10.1007/BF00481519

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