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Substituted spiro-heterocycles containing 1,2,4-triazole-3-thione, were formed at room temperature via the reaction of N-cycloalkylidene hydrazinecarbothioamides 2 with benzoas 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 benzoand naphthoquinone derivatives as well as the conversions are also presented.

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