Transformations of 3-acyl-4H-polyfluorochromen-4-ones under the action of amino acids and biogenic amines

Shcherbakov, Konstantin V. ✉; Artemyeva, Mariya A.; Burgart, Yanina V.; Evstigneeva, Natalya P.; Gerasimova, Natalya A.; Zilberberg, Natalia V.; Kungurov, Nicolai V.; Saloutin, Victor I.; Chupakhin, Oleg N.

English Scientific Article (Journal Article)
Published: JOURNAL OF FLUORINE CHEMISTRY 0022-1139 226 Paper: UNSP 109354 , 13 p. 2019
  • SJR Scopus - Inorganic Chemistry: Q2
    For the first time 6,7,8-trifluoro- and 5,6,7,8-tetrafluorinated 3-benzoylflavones have been obtained. Their reactions with amino acids and biogenic amines were studied in comparison with polyfluorinated 3-acetyl-2-methylchromones. For chromones, reactions at the C-2 are preferred, which lead to the pyrone ring opening to form N-substituted aminoenketones. Whereas in the case of flavones the main route is the nucleophilic aromatic substitution of the fluorine atom at the C-7. Flavones and chromones react in the same way both with dopamine to give aminoenketones, and with proline to form 7-amino-substituted chromen-4-ones. All the reactions of chromen-4-ones are accompanied by deacylation, except ones of flavones with proline. Among the synthesized aminoenketones, compounds with high antimycotic and antibacterial action were found.
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    2021-03-05 18:11