Synthesis of some triazole,tetrazole, and tetrazine derivatives from N-β-naphthalenesulfonylbenzohydrazidoyl chlorides

A series of N-β-naphthalenesulfonylbenzohydrazidoyl chlorides 8a-d has been prepared by the action of thionyl chloride on the corresponding hydrazides 7a-d . Treatment of 8 with triethylamine and morpholine afforded the tetrazines 10 and the amidrazones 11 respectively. Acid hydrolysis of 11 yielded the hydrazides 7 . Reaction of 8 with phenylhydrazine gave 3,5-diaryltetrazoles 14 . However, reaction of 8 with aroylhyrazines yielded 3,5-diaryl-4-β-naphthalenesulfonylamino-4H-1,2,4-triazoles 15 . The structures of the products were assigned upon the basis of their spectra, elemental analyses and alternate synthesis whereever possible.