Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2008, Issue 14, Pages 2430-2438Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200800123
Keywords
acidity constants; amide-hydroxyimine tautomerism; 3-fluoro-2(1H)-quinolinones; keto-enol tautomerism; Knorr-Effenberger cyclizations
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One dozen of tailormade model 3-fluoro-2(1H)-quinolinones were synthesized, in order to be investigated by UV-, IR- and NMR spectroscopic techniques. All of these compounds were found to exist predominantly, if not exclusively, in the lactam (carboxamide, 1,2-dihydro-2-oxoquinoline) form. No tautomeric lactim (iminol, azaphenol) structure was detected. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).
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