J. Bohrisch et al., SYNTHESES OF S,N-HETEROCYCLES FROM N-THIOACYLLACTAMIMINES, Phosphorus, sulfur and silicon and the related elements, 84(1-4), 1993, pp. 253-256
Nitrile imines undergo cycloadditions to the thiocarbonyl group of N-t
hioacyllactamimines 1 giving 1,3,4-thiadiazolines 2. Depending on the
substituents oxidation of N-thioacyllactamimines 1 leads to different
products, such as condensed 5-amino-1,2,4-thiadiazolium bromides 5, 3,
5-diaryl-1,2,4-dithiazolium salts 6, 3,5-diaryl-1,2,4-thiadiazoles 7 o
r 2-benzothiazolyliminopyrrolidine 8.