Springer Nature is making SARS-CoV-2 and COVID-19 research free. View research | View latest news | Sign up for updates

Synthesis of trichloro-1,4-benzoquinonyl-substituted 2,2′-bithiazoles


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.


  1. 1.

    R. E. Valter, G. A. Karlivan, M. F. Utinan, and Yu. V. Gulbis,Sib. Khim. Zh., No. 4, 39 (1992).

  2. 2.

    R. Valters, G. Karlivans, J. Gulbis, M. Utinans, and A. Bace,Phosphorus Sulfur Silicon Relat. Elem.,95–96, 457 (1994).

  3. 3.

    R. Valters, E. Liepins, G. Karlivans, V. R. Zin'kovskaya, and M. F. Utinan,Zh. Org. Khim.,21, 436 (1985).

  4. 4.

    S. Hünig, D. Scheutzow, H. Schlaf, and H. Quast,Liebigs Ann. Chem.,765, 110 (1972).

  5. 5.

    G. V. Tormos, O. J. Neilands, and M. P. Cava,J. Org. Chem.,57, 1008 (1992).

  6. 6.

    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).

  7. 7.

    M. A. Utinan, R. E. Valter, G. A. Karlivan, E. E. Liepinsh, and A. S. Edzhinya,Khim. Geterotsikl. Soedin., No. 5, 692 (1988).

Download references

Additional information

Riga Technical University, Riga LV-1048, Latvia, Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 988–992, July, 1999.

Rights and permissions

Reprints and Permissions

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

Download citation


  • Sulfate
  • Organic Chemistry
  • Dimethyl
  • FeCl3
  • Furan