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The synthesis and biological evaluation of A- and B-ring fluorinated flavones and their key intermediates
- Source :
- Journal of Fluorine Chemistry. 249:109857
- Publication Year :
- 2021
- Publisher :
- Elsevier BV, 2021.
-
Abstract
- An efficient three-step method for the synthesis of new polyfluoroflavones has been proposed using substituted benzoyl chlorides and 2-hydroxyacetophenone to form the initial 2-(polyfluoroaroyloxy)acetophenones, which are transformed into 1,3-diaryl-1,3-diketones as a result of the Baker-Venkataraman rearrangement. The ability of these 1,3-diketones to undergo keto-enol and ring-chain tautomerism was found, depending on the nature of the solvent. Under acid- or base-catalyzed conditions the alternative cyclization routes of fluorine-containing 1,3-diaryl-1,3-diketones into A- and B-ring halogenated flavones have been reported. The anti-influenza and fungistatic effects of the synthesized compounds were evaluated, and products with promising antimicrobial properties were found.
Details
- ISSN :
- 00221139
- Volume :
- 249
- Database :
- OpenAIRE
- Journal :
- Journal of Fluorine Chemistry
- Accession number :
- edsair.doi...........f8da2245959cd9c8d3915a0382fbfaae