The chemistry of o-phenylenedi-isothiocyanate. Part 3. Studies on the syntheses of heterocyclic compounds

Abstract

o-Phenylenedi-isothiocyanate (1) reacts with sodium azide to give [1,2,4]thiadiazolo[4,5a]benzimidazole-3-thione (2), which undergoes alkylation to the S-alkyl derivatives (5a–d). With N-(4-chlorophenyl)-SS-dimethylsulphimide the di-isothiocyanate (1) yields the corresponding N-arylthiadiazolo-derivative (7). Alcohols and thiophenol react with (1) and give alkoxy- or (arylthio)-thiocarbonylbenzimidazolinethiones (9a and b) and (10). The di-isothiocyanate also reacts with chloromethanesulphonamide and yields a dithiadiazepine S-dioxide (13) along with benzimidazolyl disulphide (12).