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Synthesis 2001(16): 2495-2499
DOI: 10.1055/s-2001-18720
PAPER
© Georg Thieme Verlag Stuttgart · New York

Oxidation of 2- and 3-Halogenated Quinolines: An Easy Access to 5- and 6-Halogenopyridine-2,3-dicarboxylic Acids

Marie-Delphine Le Basa, Caroline Guéretb, Cécile Perrio*a, Marie-Claire Lasnea, Louisa Barré*b
Laboratoire de Chimie Moléculaire et Thioorganique, CNRS UMR 6507, Institut des Sciences de la Matière et du Rayonnement, Université de Caen-Basse Normandie, 6 Boulevard Maréchal Juin, 14050 Caen Cedex, France
Fax: +33(2)31452877; e-Mail: perrioc@ismra.fr;
Groupe de Développements Méthodologiques en Tomographie d"Emission de Positons, LRA10V-UPRES EA 2609, CEA/DSV, Université de Caen-Basse Normandie, Centre Cyceron, 15 Boulevard Henri Becquerel, 14074 Caen Cedex, France
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Publication History

Received 27 July 2001
Publication Date:
05 August 2004 (online)

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Abstract

Pyridine-2,3-dicarboxylic acids bearing an halogen in the position α or β to the nitrogen atom were synthesized by oxidation of the corresponding quinolines. Two methods, using either ozone followed by hydrogen peroxide or ruthenium tetroxide under catalytic conditions were used. Diacids 1b,c and 2a-c substituted in 6-position by a chlorine or bromine and in 5-position by a fluorine, chloride or bromine, respectively, were isolated in yields ranging from 46-71%. Yields of 6-fluoro and 6- or 5-iodo diacids 1a,d and 2d did not exceed 30%.

Key words

oxidation - quinolines - pyridine-2,3-dicarboxylic acids - halogens - ozonolysis - ruthenium tetroxide