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.
This is a preview of subscription content, log in to check access.
Buy single article
Instant access to the full article PDF.
Price includes VAT for USA
Subscribe to journal
Immediate online access to all issues from 2019. Subscription will auto renew annually.
This is the net price. Taxes to be calculated in checkout.
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).
Riga Technical University, Riga LV-1048, Latvia, Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 988–992, July, 1999.
About this article
Cite this article
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
- Organic Chemistry