Chemistry of Heterocyclic Compounds

, Volume 20, Issue 4, pp 367–370 | Cite as

Research in the chemistry of heterocyclic quinoneimines. 5. Effect of benzannelation of phenothiazin-3-one on its reaction with O- and S-nucleophiles

  • V. I. Vysokov
  • G. B. Afanas'eva
  • O. N. Chupakhin
  • I. S. Ufimtseva


Benzo[a]phenothiazin-5-one reacts with alkoxides, thiols, or thiolates to give 6-alkoxy- and 6-alkyl(aryl)thiobenzo[a]phenothiazin-5-ones, respectively. Benzannelation of phenothiazin-3-one in the quinoneimine fragment markedly hinders reactions with O- and S-nucleophiles with retention of the reaction center in the quinoneimine fragment of the molecule.


Organic Chemistry Thiol Reaction Center Alkoxide Thiolates 
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.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    G. B. Afanas'ev, V. I. Vysokov, O. N. Chupakhin, T. K. Pashkevich, and E. O. Sidorov, Khim. Geterotsikl. Soedin., No. 3, 334 (1984).Google Scholar
  2. 2.
    A. Dienes, Appl. Phys., 7, 135 (1975).Google Scholar
  3. 3.
    G. Mann, S. Hauptmann, H. Wilde, J. Lehmann, and M. Neumann, East German Patent No. 139268.Google Scholar
  4. 4.
    D. A. Shirley, J. S. Gilmer, and W. D. Waters, J. Chem. Soc., 5260 (1964).Google Scholar
  5. 5.
    N. L. Agarwal and R. L. Mital, Indian J. Chem., 14B, 381 (1976).Google Scholar
  6. 6.
    Y. Ueno, Y. Takeuchi, J. Koshitani, and T. Yoshida, J. Heterocycl. Chem., 19, 167 (1982).Google Scholar
  7. 7.
    Y. Ueno, H. Shiraki, J. Koshitani, and T. Yoshida, Synthesis, No. 4, 313 (1980).Google Scholar
  8. 8.
    G. B. Afanas'eva, K. I. Pashkevich, I. Ya. Postovskii, V. G. Vykhristyuk, N. P. Shimanskaya, and V. D. Bezuglyi, Khim. Geterotsikl. Soedin., No. 10, 1345 (1972).Google Scholar
  9. 9.
    G. B. Afanas'eva, V. I. Vysokov, T. K. Pashkevich, and O. N. Chupakhin, Khim. Geterotsikl. Soedin., No. 2, 214 (1983).Google Scholar
  10. 10.
    N. L. Agarval and R. L. Mital, J. Chem. Eng. Data, 20, 199 (1975).Google Scholar

Copyright information

© Plenum Publishing Corporation 1984

Authors and Affiliations

  • V. I. Vysokov
    • 1
  • G. B. Afanas'eva
    • 1
  • O. N. Chupakhin
    • 1
  • I. S. Ufimtseva
    • 1
  1. 1.S. M. Kirov Ural Polytechnic InstituteSverdlovsk

Personalised recommendations