2-Chloro-4,5-dihydroimidazole. Part VII. Reactions with carbon disulfide and potassium O-alkyl dithiocarbonates. Synthesis and transformations of 2,3,7,8-tetrahydro-5H-diimidazo[2,1-b : 1′,2′-e][1,3,5]thiadiazine-5-thione

Abstract

2-Chloro-4,5-dihydroimidazole 1 reacted with carbon disulfide to give 2,3,7,8-tetrahydro-5H-diimidazo[2,1-b : 1′,2′-e][1,3,5]thiadiazine-5-thione 5. Acid hydrolysis of 5 gave imidazolidine-2-thione 6, which reacted with amines, dialkylhydrazines, and alkoxides to give thioureas 9, thiosemicarbazides 10 and thiocarbamates 11, respectively. Reaction of the hemisulfate of 1 with excess of potassium O-alkyl dithiocarbonates afforded diesters of thiodicarbonic acid 13.