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Limitations of the Wittig-Horner-type annulation of fluorobutenolide moiety to 3-hydroxyquinoline-2,4(2H,3H)-diones. Novel modifications of the Perkow reaction including fluorinated acyloxy leaving groups |
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| Authors: | Karel Pomeisl Jaroslav Kví?ala Antonín Klásek Vladislav Kubelka Jan ?ejka |
| Institution: | a Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10 Prague, Czech Republic b Department of Organic Chemistry, Prague Institute of Chemical Technology, Technická 5, 166 28 Prague 6, Czech Republic c Enviromental Department of Chemistry and Environmental Technology, Tomáš Bat'a University, Nám. TGM 275, 762 72 Zlín, Czech Republic d Zentiva, U Kabelovny 130, 102 37 Prague 10, Czech Republic e Department of Solid State Chemistry, Prague Institute of Chemical Technology, Technická 5, 166 28 Prague 6, Czech Republic |
| Abstract: | 3-(Fluoroacyloxy)quinoline-2,4(1H,3H)-diones react with triethyl phosphite to afford either the product of the Perkow reaction or the corresponding 4-ethoxyquinolin-2(1H)-one. In both reactions, the fluorocarboxylate anion acts as the leaving group. For the corresponding 3-(fluoroiodoacetoxy) derivative this observation precludes the application of the intramolecular Wittig-Horner synthesis to modify quinoline-2,4(1H,3H)-diones by the annulation of a fluorinated but-2-enolide moiety. |
| Keywords: | Wittig-Horner synthesis Lithium 2-(diethoxyphosphoryl)-2-fluoroacetate 3-Halogenoacyloxyquinoline-2 4(1H 3H)-diones Fluorofuranone But-2-enolide Perkow reaction 19F NMR reaction profile Cytostatic activity Chronic myeloid leukemia Breast carcinoma |
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