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Russian Chemical Bulletin

, Volume 48, Issue 8, pp 1537–1541 | Cite as

Reactions of ethyl 5,6,7,8-tetrafluoro-2-methylchromone-3-carboxylate and 3-acetimidoyl-5,6,7,8-tetrafluoro-4-hydroxycoumarin with S-nucleophiles

  • I. T. Bazyl'
  • S. P. Kisil'
  • S. N. Frolov
  • Ya. V. Burgart
  • V. I. Saloutin
Organic Chemistry

Abstract

The reactions of ethyl 5,6,7,8-tetrafluoro-2-methylchromone-3-carboxylate with mercaptoacetic acid and 1,2-ethanedithiol afforded C(7)-substitution products. The above-mentioned chromone reacted with 2-mercaptoethanol to yield 7-mono- or 5,7,8-trisubstituted products depending on the reaction conditions. The reaction of 3-acetimidoyl-5,6,7,8-tetrafluoro-4-hydroxycoumarin with 2-mercaptoethanol afforded a 5,7,8-trisubstituted produect. The acyl-lactone rearrangement of mono- and trisubstituted chromones yielded the corresponding coumarins.

Key words

chromones coumarins S-nucleophiles substitution acyl-lactone rearrangement 

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Copyright information

© Kluwer Academic/Plenum Publishers 1999

Authors and Affiliations

  • I. T. Bazyl'
    • 1
  • S. P. Kisil'
    • 1
  • S. N. Frolov
    • 1
  • Ya. V. Burgart
    • 1
  • V. I. Saloutin
    • 1
  1. 1.Institute of Organic SynthesisUral Branch of the Russian Academy of SciencesEkaterinburgRussian Federation

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