2′-Hydroxyflavylium: introducing flavanones into the flavylium network of chemical reactions

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Abstract

Chalcones possessing a hydroxyl group in position 2 cyclize to form flavylium salts in acidic media, this reaction being reversible under neutral-basic conditions. On the other hand, chalcones possessing a hydroxyl group in position 2′ cyclize to form flavanones in basic media. By synthesizing 2′-hydroxyflavylium tetrafluoroborate, it was possible to obtain trans-2,2′-dihydroxychalcone that in solution can evolve to 2′-hydroxyflavanone or back to 2′-hydroxyflavylium depending on the pH. The several equilibria established in aqueous solution were fully characterized. The importance of including flavanones into the flavylium network of chemical reactions is briefly exploited.

Original languageEnglish
Pages (from-to)714-720
Number of pages7
JournalTetrahedron
Volume64
Issue number4
DOIs
Publication statusPublished - 21 Jan 2008

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