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Eschenmoser Coupling Reaction and Reactivity of Hydrazinecarbothioamides in the Synthesis of Benzindazole and Naphthothiazole Derivatives
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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.
Georg Thieme Verlag KG
Title: Eschenmoser Coupling Reaction and Reactivity of Hydrazinecarbothioamides in the Synthesis of Benzindazole and Naphthothiazole Derivatives
Description:
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.
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