37932-51-7Relevant articles and documents
Synthesis of Annelated 1,3,4,6-Thiatriazepines from Reaction of Cyclic Thioureas with 1,4-Dichloro-2,3-diazabutadienes
Moss, Stephen F.,Taylor, David R.
, p. 1999 - 2006 (2007/10/02)
Acyclic thioureas react with 1,4-dichloro-1,4-diphenyl-2,3-diazabutadiene in the presence of triethylamine or sodium hydride to give mainly 2,5-diphenyl-1,3,4-thiadiazole.By contrast, the cyclic thioureas imidazoline-2-thione, dihydropyrimidine-2-thione, 4-oxopyrimidine-2-thione, 6-methyl-4-oxopyrimidine-2-thione, and benzimidazole-2-thiol, react with 1,4-dichloro-1,4-diphenyl-2,3-diazabutadiene, and, in the case of imidazoline-2-thione, also with 1,4-dichloro-1,4-bis(4-chlorophenyl)-2,3-diazabutadiene, in the presence of a two-molar proportion of sodium hydride, to give the series of 2,5-diphenyl--1,3,4,6-thiatriazepines: (7a) (35percent), (7b) (63percent), (9a) (36percent), (9b) (26percent), (98) (49percent), and (7c) (29percent), respectively.Formation of the thiatriazaepines is accompanied by variable amounts of 2,5-diaryl-1,3,4-thiadiazoles (2a,b).Acid hydrolysis of the diarylthiatriazepines yields a mixture of breakdown products, of which the principal components are the diphenylthiadiazole (2a) (12-90percent), 2,5-diphenyl-1,3,4-oxadiazole , the corresponding thione (21-22percent), and, from the thiatriazepinones (9a and b), the corresponding pyrimidinediones (15a and b) (81-95percent).The thiatriazepine (7a) reacts with sodium ethoxide to give a ring-opened product, believed to be 1-ethoxy-4-(2-thioxoimidazolin-1-yl)-1,4-diphenyl-2,3-diazabutadiene (18) (77percent).