Electrochemical Reduction of Flavones

Flavone and its derivatives comprise an important class of compounds due to their diverse biological properties and therapeutic applications.  They are commonly used as precursors in the preparation of various biologically active compounds, such as anticancer pharmaceuticals [1].  Dimerization of flavone may lead to new and alternative drug candidates with improved pharmacological profile.

In this work, we report electrochemical results obtained by means of cyclic voltammetry and controlled-potential electrolysis for the reduction of flavones in both aprotic and protic media containing tetraalkylammonium salts, under various experimental conditions, including an aprotic solvent (DMF) with an added proton donor.  We have identified and quantitated the various electrolysis products with the aid of GC–MS and GC.  A mechanistic pathway is proposed to account for the formation of products.

 

ACKNOWLEDGMENT

 We are grateful to the Fundação para a Ciência e Tecnologia (PestC/QUI/UI0686/2013 and FCOMP-01-0124-FEDER-037302) for financial support of this work.

 

REFERENCE

 [1] R. H. Greg, R. H. James, J. Biol. Chem. 1997, 272, 5396.