Synthèse de tétrahydrocarbazolones et application à la préparation d'analogues hétérocycliques des pyrido-carbazoles

Abstract : Many studies toward the synthesis of pyridocarbazoles alkaloïds like ellipticine and olivacine have been made in recent years. However, few examples of the replacement of the pyridine ring in the natural structure by other heteroaromatic systems have been described. Using the reactivity of the ketone moiety in the tetrahydrocarbazolones, we have built up several heterocycles condensed to the carbazole moiety. In the first part, we describe the preparation of the tetrahydrocarbazolones by Fischer indole synthesis, starting from cyclohexanediones or méthyl-cyclihexanediones. Studies of the indolisation conditions allowed improvement in the results of the Fischer cyclisation and also access to the methyl- and dimethyl-tetrahydrocarbazolones. In the second part, we develop the preparation of the pyridocarbazoles analogues. Thus, the synthesis of furo-, thieno-, seleno-, pyrazolo- and selenadiazolo- annelated carbazoles ares presented
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Delphine Joseph. Synthèse de tétrahydrocarbazolones et application à la préparation d'analogues hétérocycliques des pyrido-carbazoles. Autre. Université Paul Verlaine - Metz, 1995. Français. ⟨NNT : 1995METZ033S⟩. ⟨tel-01777089⟩

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