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.

Authors: G. A. Karlivan, R. E. Valter, and A. E. Bace.

English Translation in Chemistry of Heterocyclic Compounds, 1999, 35 (7), pp 866-870

http://link.springer.com/article/10.1007/BF02252114