Abstract
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.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
G. B. Afanas'ev, V. I. Vysokov, O. N. Chupakhin, T. K. Pashkevich, and E. O. Sidorov, Khim. Geterotsikl. Soedin., No. 3, 334 (1984).
A. Dienes, Appl. Phys., 7, 135 (1975).
G. Mann, S. Hauptmann, H. Wilde, J. Lehmann, and M. Neumann, East German Patent No. 139268.
D. A. Shirley, J. S. Gilmer, and W. D. Waters, J. Chem. Soc., 5260 (1964).
N. L. Agarwal and R. L. Mital, Indian J. Chem., 14B, 381 (1976).
Y. Ueno, Y. Takeuchi, J. Koshitani, and T. Yoshida, J. Heterocycl. Chem., 19, 167 (1982).
Y. Ueno, H. Shiraki, J. Koshitani, and T. Yoshida, Synthesis, No. 4, 313 (1980).
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).
G. B. Afanas'eva, V. I. Vysokov, T. K. Pashkevich, and O. N. Chupakhin, Khim. Geterotsikl. Soedin., No. 2, 214 (1983).
N. L. Agarval and R. L. Mital, J. Chem. Eng. Data, 20, 199 (1975).
Author information
Authors and Affiliations
Additional information
See [1] for Communication 4.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 460–463, April, 1984.
Rights and permissions
About this article
Cite this article
Vysokov, V.I., Afanas'eva, G.B., Chupakhin, O.N. et al. Research in the chemistry of heterocyclic quinoneimines. 5. Effect of benzannelation of phenothiazin-3-one on its reaction with O- and S-nucleophiles. Chem Heterocycl Compd 20, 367–370 (1984). https://doi.org/10.1007/BF00513846
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00513846