Abstract
The corresponding 6-arylamino derivatives were obtained by reaction of 6-chloro, 6-bromo, and 6-methoxy derivatives of benzo-1,2,3-dithiazolium and their selenium analogs — benzo-1,2,3-thiaselenazolium, benzo-2,1,3-thiaselenazolium, and benzo-1,2,3-diselenazolium salts — with aromatic amines. The 6-methoxy derivatives also react with acetates of secondary aliphatic amines, whereas in the case of the chloro derivatives attack is directed to the heteroring. 6-Aryl(dialkyl)amino derivatives of dithiazolium and 1,2,3-thiaselenazolium salts are protonated in concentrated sulfuric acid at the exocyclic nitrogen atom. The analogous derivatives of 2,1,3-thiaselenazolium and diselenazolium salts under the same conditions form a tautomeric mixture of dications, the position of the equilibrium between which depends on the substituent. The electronic and PMR spectra of the amination products are presented.
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B. Kh. Strelets, L. S. Éfros, and Yu. I. Akulin, Khim. Geterotsikl. Soedin., No. 2, 183 (1976).
H. E. Fierz-David, J. Soc. Dyers Colourists, 51, 50 (1935).
Yu. I. Akulin, B. Kh. Strelets, and L. S. Éfros, Khim. Geterotsikl. Soedin., No. 1, 138 (1974).
Yu. I. Akulin, B. Kh. Strelets, and L. S. Éfros, Khim. Geterotsikl. Soedin., No. 2, 275 (1975).
Yu. I. Akulin, B. Kh. Strelets, and L. S. Éfros, Khim. Geterotsikl. Soedin., No. 10, 1429 (1975).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1499–1502, November, 1977.
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Akulin, Y.I., Strelets, B.K. & Éfros, L.S. Reactions of benzo-1,2,3-dithiazolium salts and their selenium analogs with amines. Chem Heterocycl Compd 13, 1198–1201 (1977). https://doi.org/10.1007/BF00475944
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DOI: https://doi.org/10.1007/BF00475944