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Thiosemicarbazides 1a–c reacted with tetracyanoethene 2 in ethyl acetate with admission of air to form the 7-amino-2-organylimino-2,3-dihydro-1,3,4-thiadiazepine-5,6-dicarbonitriles 6a,b, 7amino-1-organylimino-3-oxopyrazolo[1,2-c]-1,3,4-thiadiazole-5,5,6-tricarbonitriles 7a–c, 7amino-1-organyl-iminopyrazolo[1,2-c]-1,3,4-thiadiazole-3,3,5,5,6-pentacarbonitriles 8a–c and 3amino-1H-pyrazole-4,5-dicarbonitriles (9) in moderate yields. Rationales for the observed conversations are presented.

Pyrazole, pyrazolo[1,2-c]-1,3,4-thiadiazole and thiadiazepine derivatives from thiosemicarbazides