Abstract
The reaction of thiourea of N-substituted thioureas with 2-(2-N,N-diethylaminoethenyl)-3,5,6-trichloro-1,4-benzoquinone leads, through the formation of 2,5-dihydroxy-3,4,6,7-tetrachlorocoumaran, to 2-amino-5-(2,5-dihydroxy-3,4,6-trichlorophenyl)thiazoles (which exist in the form of betaines), the oxidation of which leads to 2-amino-5-(3,5,6-trichloro-1,4-benzoquinon-2-yl)thiazoles.
Similar content being viewed by others
Literature Cited
I. B. Torrance, I. I. Mayerle, V. Y. Loe, and K. Bechgaard, J. Am. Chem. Soc.,101, 4747 (1979).
D. Buckley, H. B. Henbest, and P. Slade, J. Chem. Soc.,12, 4891 (1957).
R. é. Valter, é. é. Liepin'sh, F. A. Karlivan, V. R. Zin'kovska, and M. F. Utinan, Zh. Org. Khim.,21, 436 (1985).
G. A. Karlivan, R. é. Valter, and M. F. Utinan, USSR Author's Certificate No. 1188169; Byull. Izobret., No. 70, 82 (1985).
G. A. Karlivan, R. é. Valter, and M. F. Utinan, USSR Author's Certificate No. 1131874; Byull. Izobret., No. 48, 87 (1984).
St. Berger and A. Rieker, in: The Chemistry of the Quinonoid Compounds, ed. S. Patai, Wiley, New York-London (1974), Part 1, p. 163.
Yu. N. Sheinker, V. V. Kushkin, and I. Ya. Postovskii, Zh. Fiz. Khim.,31, 214 (1957).
Yu. N. Sheinker, I. Ya. Postovskii, N. M. Voronina, and V. V. Kushkin, Zh. Fiz. Khim.,31, 1744 (1957).
S. G. Bogomolov, Yu. N. Sheinker, and I. Ya. Postovskii, Dokl. Akad. Nauk SSSR,93, 277 (1953).
G. Toth and B. Podanyi, J. Chem. Soc., Perkin Trans. 2, No. 1, 91 (1984).
G. J. Martin, M. L. Martin, and I. P. Gouesnard,15N NMR Spectroscopy, Springer Verlag, Berlin (1981), p. 223.
J. Elguero, C. Marzin, A. Katritzky, and P. Linda, in: The Tautomerism of Heterocycles, eds. A. R. Katritzky and A. I. Boulton, Academic Press, New York (1976), p. 427.
J. Q. Chambers, in: The Chemistry of the Quinonoid Compounds, ed. S. Patai, Wiley, New York-London (1974), Part 2, p. 737.
A. Bax, R. H. Griffey, and B. L. Hawkins, J. Magn. Reson.,55, 301 (1983).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 692–698, May, 1988.
Rights and permissions
About this article
Cite this article
Utinan, M.F., Valter, R.É., Karlivan, G.A. et al. Synthesis and properties of 2-amino-5-(3,5,6-trichloro-1,4-benzoquinon-2-yl)thiazoles. Chem Heterocycl Compd 24, 567–573 (1988). https://doi.org/10.1007/BF00755701
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00755701