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

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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Additional information

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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Keywords

  • Sulfate
  • Organic Chemistry
  • Dimethyl
  • FeCl3
  • Furan