1,5-Dihydro-1,2,3,4-thia(SIV)triazoles from quaternary salts of NN-disubstituted thioamides and sodium azide

Abstract

Quaternary salts [e.g.(I)] of disubstituted thioamides react with aqueous sodium azide at room temperature giving high yields of products which are probably 1,5,5-trisubstituted 1,5-dihydro-1,2,3,4-thia(S^IV)triazoles [e.g.(III)]. These are decomposed by dilute acids with loss of nitrogen giving amidines [e.g.(VII)] and thiosulphinic S-esters [e.g.(VIII)]. When the thiatriazole (III) is heated in solution in toluene or cyclohexene, the dithioacetal of benzaldehyde or cyclohex-2-enone (respectively) is formed.