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Synthesis and transformations of 1-methyl-4-azafluorene

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

By means of catalytic dehydrocyclization of dimethyl-substituted 2-phenylpyridines in a pyridine ring to 1(2,3)methyl-4-azafluorenes with subsequent oxidation, synthesis of alkaloid onychine — 1-methyl-4-azafluorene — several of its isomers were achieved. Using 1-methyl-4-azafluorene, we obtained a C9 furfurylidene product, substituted tetrahydroindine[1,2-b]pyridine and NH-indine[1,2-b]-pyridine. We obtained 7-nitro-1-methyl-4azafluorene by nitration of onychine and oxidation of nitro-substituted azafluorene; this indicates an identical orientation of 4-azafluoren(one) and fluoren(one) during nitration.

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Literature cited

  1. M. E. L. de Almeida, F. R. Braz, V. Buelow, O. R. Gottlieb, and I. G. S. Maia, Phytochemistry, 15, 1186 (1976).

    Google Scholar 

  2. I. Koyama, T. Sugito, and I. Suzuta, Heterocycles, 12, 1017 (1979).

    Google Scholar 

  3. B. F. Bowden, K. Picker, E. Ritchie, and W. C. Taylor, Aust. J. Chem., 28, 2685 (1975).

    Google Scholar 

  4. N. S. Prostakov, V. G. Pleshakov, T. S. Seitembetov, D. A. Fesenko, and L. O. Onasan'ya, Zh. Org. Khim., 13, 1484 (1977).

    Google Scholar 

  5. A. E. Chichibabin and D. I. Orochko, Zh. Russk. Khim. Obshchestva, 62, 1201 (1930).

    Google Scholar 

  6. A. T. Soldatenkov, V. O. Fedorov, R. Chandra, V. M. Polosin, A. I. Mikaya, and N. S. Prostakov, Zh. Org. Khim., 16, 188 (1980).

    Google Scholar 

  7. N. S. Prostakov, K. D. Mat'yu, and V. A. Kurichev, Khim. Geterotsikl. Soedin., No. 5, 876 (1967).

    Google Scholar 

  8. N. S. Prostakov, A. T. Soldatenkov, and V. O. Fedorov, Khim. Geterotsikl. Soedin., No. 8, 1101 (1979).

    Google Scholar 

  9. H. Günther, NMR Spectroscopy, Wiley, New York (1980), p. 98.

    Google Scholar 

  10. J. M. Bonnier and J. Court, Bull. Soc. Chim. France, No. 1, 142 (1970).

    Google Scholar 

  11. I. N. Chatterjea and K. Prasad, J. Indian Chem. Soc., 32, 371 (1955).

    Google Scholar 

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Authors and Affiliations

  1. Patrice Lumumba International-Friendship University, 117923, Moscow

    N. S. Prostakov, A. T. Soldatenkov, P. K. Radzhan, V. O. Fedorov, A. A. Fomichev & V. A. Rezakov

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  1. N. S. Prostakov
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  2. A. T. Soldatenkov
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  3. P. K. Radzhan
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  4. V. O. Fedorov
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  5. A. A. Fomichev
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  6. V. A. Rezakov
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 513–517, April, 1982.

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Prostakov, N.S., Soldatenkov, A.T., Radzhan, P.K. et al. Synthesis and transformations of 1-methyl-4-azafluorene. Chem Heterocycl Compd 18, 390–394 (1982). https://doi.org/10.1007/BF00503560

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  • DOI: https://doi.org/10.1007/BF00503560

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