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Chemistry of Heterocyclic Compounds

, Volume 14, Issue 11, pp 1217–1223 | Cite as

Indole derivatives

CXVII. Reaction of 3-aminoindoles with carbon disulfide. Convenient one-step synthesis of 3-indolyl isothiocyanates and indolo[2,3-d]-1,3-thiazines
  • V. S. Velezheva
  • A. V. Yarosh
  • T. A. Kozik
  • N. N. Suvorov
Article

Abstract

A new one-step method was developed for the preparation of 3-indolyl isothiocyanates by reaction of 3-aminoindoles with carbon disulfide in the presence of sodium ethoxide. It is shown that indolo[2,3-d]-1,3-thiazines are obtained from 3-aminoindoles and carbon disulfide when extraneous bases are absent. The structures of the compounds are confirmed by data from their IR, UV, PMR, and mass spectra.

Keywords

Sodium Mass Spectrum Organic Chemistry Disulfide Indole 
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.
    V. S. Velezheva, V. N. Gunar, M. V. Balyakina, and N. N. Suvorov, Khim. Geterotsikl. Soedin., No. 7, 939 (1978).Google Scholar
  2. 2.
    T. Takeshima, N. Fukada, M. Muraoka, and T. Miyauchi, J. Synth. Org. Chem., Jpn., 31, 811 (1973).Google Scholar
  3. 3.
    T. Takeshima, T. Miyauchi, N. Fukada, and S. Koshisava, J. Chem. Soc., Perkin I, No. 10, 1009 (1973).Google Scholar
  4. 4.
    J. Taminaga, C. Tamora, S. Sato, T. Hata, R. Natsuki, J. Matsuda, and J. Kobayashi, Chem. Pharm. Bull, 21, 1651 (1973).Google Scholar
  5. 5.
    J. Taminaga, J. Matsuda, and J. Kobayashi, J. Pharm. Soc. Jpn., 95, 980 (1975).Google Scholar
  6. 6.
    W. Braun, Ber., 36, 3520 (1903).Google Scholar
  7. 7.
    E. Hodkins and W. P. Reeves, J. Org. Chem., 29, 3098 (1964).Google Scholar
  8. 8.
    A. V. Yarosh, V. S. Velezheva, T. A. Kozik, and N. N. Suvorov, Khim. Geterotsikl. Soedin., No. 4, 481 (1977).Google Scholar
  9. 9.
    A. Albert and E. Serjeant, Ionization Constants of Acids and Bases, Methuen (1962).Google Scholar
  10. 10.
    R. Reynaud, Bull. Soc. Chim. France, No. 12, 4957 (1967).Google Scholar
  11. 11.
    T. Takeshima, T. Hayauchi, M. Muraoka, and T. Matsuoka, J. Org. Chem., 32, 980 (1967).Google Scholar
  12. 12.
    G. L. Garraway, J. Chem. Soc., B, No. 1, 92 (1966).Google Scholar
  13. 13.
    L. Kaluza, Monatsh., 33, 964 (1912).Google Scholar
  14. 14.
    S. Sakai, F. Fryinami, and F. Aisawa, Bull. Chem. Soc. Jpn., 48, 2981 (1975).Google Scholar
  15. 15.
    J. S. Johovi, U. Agarawala, and P. B. Rao, Indian J. Chem., 8, 759 (1970).Google Scholar

Copyright information

© Plenum Publishing Corporation 1979

Authors and Affiliations

  • V. S. Velezheva
    • 1
  • A. V. Yarosh
    • 1
  • T. A. Kozik
    • 1
  • N. N. Suvorov
    • 1
  1. 1.D. I. Mendeleev Moscow Institute of Chemical TechnologyMoscow

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