Eschenmoser Coupling Reaction and Reactivity of Hydrazinecarbo­thioamides in the Synthesis of Benzindazole and Naphthothiazole Derivatives

Abstract

N-Unsubstituted and N-substituted 2-phenylhydrazinecarbothioamides react with 2,3-dichloro-1,4-naphthoquinone to give a series of unprecedented 3-amino- and 3-(alkylamino)-1-phenyl-1H-benzo[f]indazole-4,9-diones in good yields. On the other hand, the reaction of N-substituted 2-tosylhydrazinecarbothioamides with 2,3-dichloro-1,4-naphthoquinone afforded (Z)-N-[3-(tosylamino)-4,9-dioxo-4,9-dihydronaphtho[2,3-d]thiazol-2(3H)-ylidene]-substituted aminium chlorides and (Z)-N-[(2-substituted imino)-4,9-dioxo-4,9-dihydronaphtho[2,3-d]thiazol-3(2H)-yl]-4-toluenesulfonamide hydrates.

Key words

hydrazinecarbothioamides - 2,3-dichloro-1,4-naphtho­quinone - benzo[f]indazole-4,9-diones - naphtho[2,3-d]thiazoles - Eschenmoser­ reaction

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