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QUANTUM-CHEMICAL ANALYSIS OF THE ALGAR–FLYNN–OYAMADA REACTION MECHANISM

И. Э. Сердюк, А. Д. Рошаль, Е. Блажейовски
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Abstract


This work is devoted to improving the understanding of Algar–Flynn–Oyamada reaction mechanism and the analysis of factors that affect the formation of flavonols. The calculation of thermodynamic parameters for the key reaction steps pointed to a mechanism involving chalcone epoxides as intermediates. A correlation was identified between the nucleophilicity of oxygen atom at  position 2' of epoxide anions and the yields of flavonols. An increased charge at the nucleophilic center was shown to reduce the effectiveness of β-cyclization of epoxide anions.

How to Cite
Serdiuk, I. E.; Roshal, A. D.; Błażejowski, J. Chem. Heterocycl. Compd. 2014, 50, 393. [Khim. Geterotsikl. Soedin. 2014, 431.]

For this article in the English edition see DOI 10.1007/s10593-014-1487-2


Keywords


chalcone; epoxychalcone; flavonol; Algar-Flynn-Oyamada reaction; reaction mechanism

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