Beilstein Journal of Organic Chemistry (Dec 2005)

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

  • Oldřich Paleta,
  • Karel Pomeisl,
  • Stanislav Kafka,
  • Antonín Klásek,
  • Vladislav Kubelka

DOI
https://doi.org/10.1186/1860-5397-1-17
Journal volume & issue
Vol. 1, no. 1
p. 17

Abstract

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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.