A variety of 2‐pyrrolidino‐, 2‐N‐methylpiperazino‐, 2‐piperidino‐, and 2‐morpholino‐1,3,4‐thiadiazines were prepared by cyclocondensation of phenacyl halides with thiosemicarbazides. Heating of the products resulted in desulfurization and formation of pyrazoles. The rate of this process strongly depends on the substitution pattern of the 1,3,4‐thiadiazines.

Imidazo[2,1‐b][2H‐1,3,4]thiadiazines were prepared by cyclization of 2‐amino‐5‐(4‐chlorophenyl)‐6H‐1,3,4‐thiadiazine with α‐haloketones. 1,2,4‐Triazolo[3,4‐b][2H‐1,3,4]thiadiazines were prepared by cyclization of 4‐amino‐5‐sulfanyl‐l,2,4‐triazoles with phenacyl bromides.

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Synthesis and Reactivity of 2-Pyrrolidino-, 2-N-Methylpiperazino-, 2-Piperidino-, and 2-Morpholino-1,3,4-thiadiazines. -A variety of the title thiadiazine derivatives (III) are synthesized by cyclocondensation of phenacyl halides with thiosemicarbazides (I). Heating of these 1,3,4-thiadiazines results in desulfurization and formation of pyrazoles. -(KNAK, S.; PFEIFFER, W.-D.; DOLLINGER, H.; LANGER*, P.; J. Heterocycl. Chem. 52 (2015) 2, 450-462, http://dx.