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Communication | Regular issue | Vol 48, No. 6, 1998, pp.1111-1116
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8143
Regioselective Nucleophilic Substitution of Halogen Derivatives of 1-Substituted 4-Oxo-1,4-dihydroquinoline-3-carboxylic Acids

István Hermecz,* Lelle Vasvári-Debreczy, Benjamin Podányi, Géza Kereszturi, Mária Balogh, Ágnes Horváth, and Péter Várkonyi

*CHINOIN Pharmaceutical and Chemical Works Ltd., P. O. Box 110, H-1325 Budapest, Hungary

Abstract

The rate of the nucleophilic displacement of the fluoro atom of 7-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate could be enhanced either by the introduction of further fluoro atom(s) into position(s) 6 and/or 8, or by the formation of a boron chelate (e.g. 3). The regioselectivity of the nucleophilic substitution of the chloro atom in 1-substituted 6-fluoro-7-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acids could also be enhanced by the formation of a boron chelate (e.g. 7).