New modification of the Perkow reaction: halocarboxylate anions as leaving groups in 3-acyloxyquinoline-2,4(1H,3H)-dione compounds

Oldrich Paleta; Karel Pomeisl; Stanislav Kafka; Antonín Klásek; Vladislav Kubelka

doi:10.1186/1860-5397-1-17

New modification of the Perkow reaction: halocarboxylate anions as leaving groups in 3-acyloxyquinoline-2,4(1H,3H)-dione compounds

Beilstein J Org Chem. 2005 Dec 9:1:17. doi: 10.1186/1860-5397-1-17.

Authors

Oldrich Paleta¹, Karel Pomeisl, Stanislav Kafka, Antonín Klásek, Vladislav Kubelka

Affiliation

¹ Department of Organic Chemistry, Prague Institute of Chemical Technology, Technická 5, 16628 Prague 6, Czech Republic. oldrich.paleta@vscht.cz

Abstract

Substituted 3-(fluoroacyloxy)quinoline-2,4(1H,3H)-diones including 3-(fluoroiodoacetoxy) derivatives 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 first observed leaving group. This observation restricts the application of the intramolecular Horner-Wadsworth-Emmons synthesis to modify quinoline-2,4(1H,3H)-diones by the annulation of fluorinated but-2-enolide rings.