Reactions with hydrazonoyl halides .13. Synthesis of some new thiadiazoline, arylazothiazole and pyrazole derivatives

Hydrazonoyl halide 4 reacts with sodium thiophenolate and sodium benzenesulfinate to give the corresponding hydrazones 5 and 6, respectively. Also, reacts with thiourea, potassium thiocyanate and beta-ketosulfones, to give arylazothiazoles 7, thiadiazolines 9, and pyrazols 13, respectively. Compounds 19 reacts with substituted thioanilide to afford thiadiazolines 24. The structures of the newly synthesized compounds were assigned and confirmed on the basis of their elemental analyses, spectral data and alternate synthesis whenever possible.