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Russian Chemical Bulletin

, Volume 54, Issue 9, pp 2157–2162 | Cite as

Reactions of 2(3)-ethoxycarbonyl-5,6,7,8-tetrafluorochromones with methylamine

  • K. V. Shcherbakov
  • Ya. V. Burgart
  • V. I. Saloutin
Article

Abstract

2-Ethoxycarbonyl-5,6,7,8-tetrafluorochromone reacts with methylamine differently, depending on the solvent nature and the amount of the amine: in DMSO and MeCN, the fluorine atom at the C(7) atom is initially replaced and then the C(2) and/or C(9) are attacked, while in ethanol, the reaction involves the C(2) atom with opening of the pyrone ring. The reaction of 3-ethoxycarbonyl-5,6,7,8-tetrafluoro-2-methylchromone with methylamine results, regardless of the solvent, in opening of the chromone ring and the formation of intermediate ethyl 3-(3,4,5,6-tetrafluoro-2-hydroxyphenyl)-2-(1-methylamino)ethylidene-3-oxopropionate, which undergoes intramolecular cyclization to give 5,6,7,8-tetrafluoro-3-(1-methyl-amino)ethylidene-3,4-dihydro-2H-benzopyran-2,4-dione.

Key words

chromone methylamine nucleophilic substitution ring opening chromone—coumarin rearrangement 

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Copyright information

© Springer Science+Business Media, Inc. 2005

Authors and Affiliations

  • K. V. Shcherbakov
    • 1
  • Ya. V. Burgart
    • 1
  • V. I. Saloutin
    • 1
  1. 1.I. Ya. Postovsky Institute of Organic SynthesisUral Branch of the Russian Academy of SciencesEkaterinburgRussian Federation

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