Novel condensed heterocyclic derivatives of benzofuran based on 2,5-dihydroxy-3,4,6,7tetrachloro-2, 3-dihydrobenzo[b]furan

We have synthesized novel condensed heterocyclic derivatives of benzofuran by reaction of 2,5-dihydroxy3, 4, 6, 7-tetrachloro-2, 3-dihydrobenzo[b]furan (I) with 4-phenyl- and 4-methylthiosemicarbazides, diphenylthiocarbazone, and also via cyclization of 2, 5-dihydroxy-4, 6, 7-trichloro-3-(N, N-diethyldithio-carbarnoyl)-2, 3dihydrobenzo[b]furan (obtained in the reaction of benzofuran I with sodium NN-dithiocarbamate).Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 463467, April 1996.     

Synthesis of [b]-Fused Benzo[d]furano Heterocycles

In the reactions of 3,4,6,7-tetrachloro-2,5-dihydroxy-2,3-dihydrobenzo[b]furan with 4-methyl and 4-phenyl thiosemicarbazides, dithizone and sodium N,N-diethyldithiocarbamate the [b]fused benzo[d]furano heterocycles have been synthesized.     

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