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 carbo dithioates 8-10. and methyl thiocarbamates 14a-c in the presence of triethy lamine to give 2,3-dihydro-1,3,3-thiadiazoles in good yields. In contrast, hydrazonoyl bromides react with each of phenylthiourea (19a). phenylthiosem icarbazide (19b) and benzoylthiosemicarbazide (19c) afforded 5-arylazothiaz ole zole 22-24a derivatives, respectively. Structures of the new compounds were elucidated on the basis of elemental analyses, spectral data, and alte rnative methods of synthesis whenever possible.