Abstract
2,2′-Bi[5-(2,5-dihydroxy-3,4,6-trichlorophenyl)thiazole] and 6-(2,5-dihydroxy-3,4,6-trichlorophenyl)-2-imino-3,4-dihydro-4H-1,4-thiazin-3-thione are synthesized from 2,5-dihydroxy-3,4,6,7-tetrachloro-2,3-dihydrobenzo[b]furan and dithiooxalyldiamide. The products are oxidized by FeCl3 to the corresponding trichloro-1,4-benzoquinonyl-substituted sulfur-containing heterocycles. N-Methylation of 2,2′-bithiazole by dimethyl sulfate gives 2,2′-bi[5-(2,5-dihydroxy-3,4,6-trichlorophenyl)-3-methylthiazolium] bismonomethyl sulfate. The last compound is readily transformed to 2,2′-bi[5-(2-hydroxy-5-oxido-3,4,6-trichlorophenyl)-3-methylthiazolium] bisbetaine.
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References
R. E. Valter, G. A. Karlivan, M. F. Utinan, and Yu. V. Gulbis,Sib. Khim. Zh., No. 4, 39 (1992).
R. Valters, G. Karlivans, J. Gulbis, M. Utinans, and A. Bace,Phosphorus Sulfur Silicon Relat. Elem.,95–96, 457 (1994).
R. Valters, E. Liepins, G. Karlivans, V. R. Zin'kovskaya, and M. F. Utinan,Zh. Org. Khim.,21, 436 (1985).
S. Hünig, D. Scheutzow, H. Schlaf, and H. Quast,Liebigs Ann. Chem.,765, 110 (1972).
G. V. Tormos, O. J. Neilands, and M. P. Cava,J. Org. Chem.,57, 1008 (1992).
G. V. Tormos, M. G. Bakker, P. Wang, M. V. Lakshmikantham, M. P. Cava, and R. M. Metzger,J. Am. Chem. Soc.,117, 8528 (1995).
M. A. Utinan, R. E. Valter, G. A. Karlivan, E. E. Liepinsh, and A. S. Edzhinya,Khim. Geterotsikl. Soedin., No. 5, 692 (1988).
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Riga Technical University, Riga LV-1048, Latvia, Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 988–992, July, 1999.
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Karlivan, G.A., Valter, R.E. & Bace, A.E. Synthesis of trichloro-1,4-benzoquinonyl-substituted 2,2′-bithiazoles. Chem Heterocycl Compd 35, 866–870 (1999). https://doi.org/10.1007/BF02252114
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DOI: https://doi.org/10.1007/BF02252114