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Reaction of dichloroketene and sulfene with n n disubstituted alpha aminomethyleneketones synthesis of pyrano 2 3 e indazole and 1 2 oxathiino 6 5 e indazole derivatives



Reaction of dichloroketene and sulfene with n n disubstituted alpha aminomethyleneketones synthesis of pyrano 2 3 e indazole and 1 2 oxathiino 6 5 e indazole derivatives



Journal of Heterocyclic Chemistry 21(2): 361-368



The polar 1,4-cycloaddition of dichloroketene to N,N-disubstituted (E)-5-aminomethylene-1,5,6,7-tetrahydro-(1-methyl)(1-phenyl)-4H-indazol-4-ones V, prepared from 1,5,6,7-tetrahydro-(1-methyl)(1-phenyl)-4H-indazol-4-ones via the 5-hydroxymethylene derivatives, gave in good yield N,N-disubstituted 4-amino-3,3-dichloro-4,5,6,7-tetrahydro-(7-methyl)(7-phenyl)pyrano[2,3-e]indazol-2(3H)-ones VI, which are derivatives of the new heterocyclic system pyrano[2,3-e]indazole. Dehydrochlorination of VI with DBN [dibutylnitrosamine?] afforded N,N-disubstituted 4-amino-3-chloro-6,7-dihydro(7-methyl)(7-phenyl)pyrano[2,3-e]indazol-2[5H]-ones VII generally in satisfactory yield. Full aromatization with DDQ [2,3-dichloro-5,6-dicyanobenzoquinone] of VII was tried only in the case of dimethylamino derivatives, giving a moderate yield of 3-chloro-4-dimethylamino(7-methyl)(7-phenyl)pyrano[2,3-e]indazol-2(7H)-ones. Cycloaddition of sulfene to V occurred only in the case of aliphatic N-substitution to give in moderate yield 4-dialkylamino-4,5,6,7-tetrahydro-(7-methyl)(7-phenyl)-3H-1,2-oxathiino[6,5-e]indazole 2,2-dioxides, which are derivatives of the new heterocyclic system 1,2-oxathiino[6,5-e]indazole. [Some heterocyclic systems have 2H-pyran and 1,2-oxathiin rings incorporated in potential pharmacologically active molecules.].

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