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(Het)aryl Difluoromethyl-Substituted beta-Alkoxyenones: Synthesis and Heterocyclizations

Bugera, M. Y., Tarasenko, K., Kondratov, I. S., Gerus, I. I., Vashchenko, B. V., Ivasyshyn, V. E. & Grygorenko, O. O., 8-Mar-2020, In : European Journal of Organic Chemistry. 2020, 9, p. 1069-1077 9 p.

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  • (Het)aryl Difluoromethyl‐Substituted β‐Alkoxyenones: Synthesis and Heterocyclizations

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DOI

  • Maksym Ya Bugera
  • Karen Tarasenko
  • Ivan S. Kondratov
  • Igor I. Gerus
  • Bohdan V. Vashchenko
  • Viktor E. Ivasyshyn
  • Oleksandr O. Grygorenko

An efficient approach to the preparation of β-alkoxyenones bearing (het)aryl difluoromethyl substituents is described. The method included acylation of acyclic or cyclic vinyl ethers with (het)aryl difluoroacetyl chlorides. The method worked well for most substrates, except aryl-substituted derivatives bearing electron-donating groups in o- or p-positions, and heteroaromatic compounds bearing sufficiently basic nitrogen atom. Synthetic utility of (het)aryl difluoromethyl-substituted β-alkoxyenones as CCC bis-electrophiles was demonstrated by heterocyclizations with common 1,2- and 1,3-bis-nucleophiles leading to compounds with (het)aryl–CF2–(het)aryl motif, in particular (het)aryl difluoromethyl-substituted pyrazoles, isoxazoles, and pyrimidines – promising chemotypes for drug discovery.

Original languageEnglish
Pages (from-to)1069-1077
Number of pages9
JournalEuropean Journal of Organic Chemistry
Volume2020
Issue number9
Publication statusPublished - 8-Mar-2020
Externally publishedYes

    Keywords

  • Organofluorine compounds, Heterocycles, Diarylmethanes, Condensation, ETHYL BROMODIFLUOROACETATE, REGIOSELECTIVE SYNTHESIS, IONIC LIQUID, FLUORINE, DERIVATIVES, ACID, ACTIVATION, INHIBITORS, DISCOVERY, PYRIDINES

ID: 132905714