Recent Advances in 1,2,3-Dithiazole Chemistry

Abstract

The reactions of 5-arylimino-4-chloro-5H-1,2,3-dithiazoles 1 with primary and sterically less bulky secondary alkylamines in CH₂Cl₂ at 25°C gave (arylimino)-cyanomethyl alkylamino disufides and N'-(aryl)-N-alkylcyanoformamidines. However, 1 reacted with excess bulky dialkylamines to give 5-(arylimino)-4-(dialkylamino)-5H-1,2,3-dithiazoles, which reacted with hydroxide base in aqueous EtOH to give N'-arylthiocarbamoyl-N,N'-dialkyamidines, excellent starting materials for various heterocyclic compounds. However, the reactions of 4-chloro-5H-1,2,3-dithiazol-5-one 2 and its analog, -5-thione 3 with primary and secondary alkylamines gave N-alkyl- and N,N-dialkylcyanothioformamides and N-alkyl- and N,N-dialkyl-5-cyanoformyl sulfenamides, respectively, depending on the alkylamines.

KEY WORD:

• 5-(Arylimino)-4-(dialkylamino)-5H-1,2,3-dithiazoles
• (Arylimino)cyanomethyl Alkyl-amino Disulfides
• N-Alkyl S-Cyanoformyl Sulfenamides
• N'-Arylthiocarbamoyl-N,N-dialkylamidines