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

نویسندگان

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

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.

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عنوان ژورنال:
  • Beilstein Journal of Organic Chemistry

دوره 1  شماره 

صفحات  -

تاریخ انتشار 2005