(Het)aryl Difluoromethyl-Substituted beta-Alkoxyenones: Synthesis and HeterocyclizationsBugera, 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.
Research output: Contribution to journal › Article › Academic › peer-review
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.
|Number of pages||9|
|Journal||European Journal of Organic Chemistry|
|Publication status||Published - 8-Mar-2020|
- Organofluorine compounds, Heterocycles, Diarylmethanes, Condensation, ETHYL BROMODIFLUOROACETATE, REGIOSELECTIVE SYNTHESIS, IONIC LIQUID, FLUORINE, DERIVATIVES, ACID, ACTIVATION, INHIBITORS, DISCOVERY, PYRIDINES