Synthesis of Novel Hydrazonoyl Chlorides as Useful Precursor in Synthesis of New Thiadiazoles, Selenadiazoles and Triazolotriazines

The reaction of hydrazino of pyrazolopyrimidine derivatives with N-phenyl-C-acetylmethanohydrazonoyl chloride afforded the corresponding hydrazonoyl chlorides. The treatment of the obtained hydrazonoyl chlorides with both of potassium thiocyanate or potassium selenocyanate gave the corresponding 1,3,4-thiadiazol-2(3H)-imine, or the selenadiazol analog, respectively. Reaction of the hydrazonoyl chloride derivatives with 6-arylmethylene-2,3-dihydro-3-thioxo-1,2,4-triazin-5(4H)-one derivatives afforded the corresponding triazolotriazine derivatives. The chemical structures of the isolated compounds were elucidated by their spectral and elemental analyses.