Reactions with Hydrazonoyl Halides XXX: Synthesis of Some 2,3-Dihydro-1,3,4-Thiadiazoles and Unsymmetrical Azines Containing Benzothiazole Moiety

C-Benzothiazoloyl-N-arylhydrazonoyl bromides 1a,b have been caused to react with each of methyl 2-thiazolylcyanomethinecarbodithioate (2), alkyl carbodithioates 8–10, and methyl thiocarbamates 14a-c in the presence of triethylamine to give 2,3-dihydro-1,3,4-thiadiazoles in good yields. In contrast, hydrazonoyl bromides react with each of phenylthiourea (19a), phenylthiosemicarbazide (19b), and benzoylthiosemicarbazide (19c) afforded 5-arylazothiazole 22–24(a-c) derivatives, respectively. Structures of the new compounds were elucidated on the basis of elemental analyses, spectral data, and alternative methods of synthesis whenever possible.