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Synfacts 2006(2): 0113-0113
DOI: 10.1055/s-2005-924819
DOI: 10.1055/s-2005-924819
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York
Indium(III)-Mediated Synthesis of Quinoline-4-carboxylic Acid Derivatives
D. Duvelleroy, C. Perrio, O. Parisel, M.-C. Lasne*
Université de Caen-Basse Normandie and Université Pierre et Marie Curie, France
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
23. Januar 2006 (online)

Significance
Readily available 2-substituted acrylates or acrylamides undergo Povarov-like cyclization with N-arylimines to produce quinoline-4-carboxylic acid derivatives employing InCl3 under microwave activation and mild conditions. The scope of the method falls short in that reactions of compounds bearing electron-withdrawing groups in 2′- and 3′-position fail to give the expected products. 13C NMR spectroscopic as well as theoretical studies suggest that InCl3 facilitates the cyclization by acting as a chelating reagent between the two reactants.