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Chemistry of Heterocyclic Compounds

, Volume 12, Issue 5, pp 541–546 | Cite as

Reactions of 1, 5-diketones. XX. Semicyclic 1, 5-diketones in the fischer reaction

  • T. V. Moskovkina
  • M. N. Tilichenko
Article
  • 30 Downloads

Abstract

Monophenylhydrazones involving both the phenacyl carbonyl group and the ring carbonyl group are formed as intermediates in the reaction of semicyclic 1, 5-diketones of the 2-(phenacylobenzyl) cyclohexanone type with phenylhydrazine in acid media. The former undergo subsequent conversion to the corresponding substituted indoles, whereas the latter are converted to substituted 1H-2, 3, 3a, 4-tetrahydropyrido [3, 2, l-j, k] carbazoles; in addition, the corresponding 5, 6, 7, 8-tetrahydroquinoline derivatives are also partially formed.

Keywords

Organic Chemistry Carbonyl Indole Carbonyl Group Acid Medium 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Literature cited

  1. 1.
    E. S. Karaulov, A. A. Usol'tsev, and M. N. Tilichenko, Khim. Geterotsikl. Soedin., No. 4, 472 (1976).Google Scholar
  2. 2.
    H. Stobbe, J. Prakt. Chem., 86, 209 (1912).Google Scholar
  3. 3.
    T. V. Moskovkina, V. A. Kaminskii, V. I. Vysotskii, and M. N. Tilichenko, Khim. Geterotsikl. Soedin., 826 (1973).Google Scholar
  4. 4.
    A. D. Chumak, G. V. Pavel', and M. N. Tilichenko, Khim. Geterotsikl. Soedin., No. 5, 738 (1973).Google Scholar
  5. 5.
    I. N. Nazarov and E. T. Golovina, Zh. Obshch. Khim., 26, 483 (1956).Google Scholar
  6. 6.
    L. N. Borisova, N. F. Kucherova, and V. A. Zagorevskii, Khim. Geterotsikl. Soedin., No. 8, 927 (1970).Google Scholar
  7. 7.
    A. Smith and I. H. P. Utley, J. Chem. Soc., C, 1 (1970).Google Scholar
  8. 8.
    P. Julien, E. Meyer, and A. Printy, in: Heterocyclic Compounds, edited by R. Elderfield, Vol. 3, (1950–1967).Google Scholar
  9. 9.
    Y. Kanaoka, Y. Ban, K. Myashita, K. Irie, and O. Yonemitsu, Chem. Pharm. Bull, 14, 934 (1966).Google Scholar
  10. 10.
    R. T. Balaban, A. R. Katritzky, and B. Sempl, Tetrahedron, 23, 4001 (1967).Google Scholar
  11. 11.
    T. V. Moskovkina, M. N. Tilichenko, B. M. Kurilenko, and L. P. Fedyaeva-Basova, Khim.-Farmats. Zh., No. 7, 3 (1973).Google Scholar
  12. 12.
    R. S. Gill, K. B. James, F. Lions, and K. T. Potts, J. Am. Chem. Soc., 74, 4923 (1952).Google Scholar
  13. 13.
    J. S. Allen and H. K. Salans, Can. J. Res., 9, 574 (1933); Chem. Abstr., 28, 2006 (1934).Google Scholar
  14. 14.
    J. R. Merchant, J. B. Mehta, and V. B. Dasai, Ind. J. Chem., 3, 561 (1965); Chem. Abstr., 64, 157876 (1966).Google Scholar

Copyright information

© Plenum Publishing Corporation 1977

Authors and Affiliations

  • T. V. Moskovkina
    • 1
  • M. N. Tilichenko
    • 1
  1. 1.Far-Eastern State UniversityVladivostok

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