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Synlett 1999; 1999(5): 563-564
DOI: 10.1055/s-1999-2663
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Synthesis of the Novel Tetrahydro-pyrrolo[2,3-c]quinolone System by Oxidation of 1,2,3,4-Tetrahydro-β-carboline

Jean-François Carniaux* , Christiane Kan-Fan, Jacques Royer, Henri-Philippe Husson
  • *Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette, France; Fax +33(1)69 07 72 47; E-mail: husson@icsn.cnrs-gif.fr
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Publikationsdatum:
31. Dezember 1999 (online)

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The synthesis of the novel pyrrolo[2,3-c]quinolin-4-one system has been achieved from the easily available tetrahydro-β-carboline 1-carboethoxy derivative using the Winterfeldt oxidation conditions (air, t-BuOK, DMF). Modification of the C-1 substituents by replacing hydrogen or aryl with an ester moiety led to a change in the reaction pathway giving the pyrrolo[2,3-c]quinolin-4-one system instead of the pyrrolo[3,4-b]quinolin-9-one system.

tetrahydro-β-carbolines - oxidation - pyrrolo[3,4-b]quinolin-9-one - pyrrolo[2,3-c]quinolin-4-one