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Tautomerism and acidity in 4-quinolone-3-carboxylic acid derivatives

✍ Scribed by Angeles de la Cruz; José Elguero; Pilar Goya; Ana Martínez; Wolfgang Pfleiderer

Publisher
Elsevier Science
Year
1992
Tongue
French
Weight
823 KB
Volume
48
Category
Article
ISSN
0040-4020

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✦ Synopsis

hototropic tautomerkm in 4-quinolone-3-carboxylic acid derivatives has been studied with particular emphasis on the intluence of the ring substituents on the equilibrium. The techniques used include W. 1H-NMR. 13C-NMR (soluttonl and 13C-NMR CP/MAS (solid state) and semiempirical and ab tnltio calculations. The pKa values of some quinolone derivatives have been determined and correlated with data obtained fkom semiempirical methods.

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## Abstract A modification of the Gould‐Jacobs reaction, particularly useful for the preparation of N‐alkyl‐4‐quinolone‐3‐carboxylic acids, is described. Decarboxylation of these acids leads to N‐alkyl‐4‐quinolones or, in the case of N‐ethyl‐benzo[h]‐4‐quinolone‐3‐carboxylic acid, to 4‐ethoxy‐benzo