Synthesis of spiro-1,2,4-triazole-3-thiones from cycloalkanone thiosemicarbazones, and formation of a cyclic 1,2-dithione

Substituted spiro-heterocycles containing 1,2,4-triazole-3-thione, were formed at room temperature via the reaction of N-cycloalkylidene hydrazinecarbothioamides 2 with benzo- as well as naphthoquinone derivatives. 2,3-Dithioxo-1,4-naphthalene-1,4-dione was synthesized upon heating compounds 2 with 2,3-dichloro-1,4-naphthoquinone. The synthesized compounds were characterized by using different spectroscopic methods and confirmed by single crystal Xray analyses. Rationales for the role of benzo- and naphthoquinone derivatives as well as the conversions are also presented.