A Convenient Route to Quinolone-Fused Imides and Lactams: Synthesis of Pyrrolo[3,4-b]quinoline-3,9-diones and 1,3,9-triones by Oxidation of Indole Derivatives

Christophe Tratrat; Sylviane Giorgi-Renault; Henri-Philippe Husson

doi:10.1055/s-1998-1856

Synlett 1998; 1998(10): 1071-1072
DOI: 10.1055/s-1998-1856

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A Convenient Route to Quinolone-Fused Imides and Lactams: Synthesis of Pyrrolo[3,4-b]quinoline-3,9-diones and 1,3,9-triones by Oxidation of Indole Derivatives

Christophe Tratrat^* , Sylviane Giorgi-Renault, Henri-Philippe Husson

^*Laboratoire de Chimie Thérapeutique Associé au CNRS (URA 1310), Faculté des Sciences Pharmaceutiques et Biologiques, Université René Descartes, 4, avenue de l'Observatoire, 75270 Paris Cedex 06, France; Fax + 33(0)1 43 29 14 03; E-mail: husson@pharmacie.univ-paris5.fr

Abstract

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Pyrrolo[3,4-b]quinoline-3,9-diones have been obtained by Winterfeldt's oxidation (O₂, t-BuOK, DMF) of readily available N(b)-substituted tetrahydropyrido[3,4-b]indol-1-ones (tetrahydrocarbazol-1-ones). Surprisingly, the oxidation using N(b)-unsubstituted analogue as starting material afforded under the same conditions pyrrolo[3,4-b]quinoline-1,3,9-trione. The difference in reactivity was interpreted. Two unknown pyrrolo[3,4-b]quinoline-1,9-dione derivatives have been synthesized by regioselective reduction of the imide function.

indole - oxidation - pyrrolo[3,4-b]quinoline-3,9-dione - pyrrolo[3,4-b]quinoline-1,3,9-trione - pyrrolo[3,4-b]quinoline-1,9-dione

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