Synthesis and electrochemical oxidation of hybrid compounds:dihydropyridine-fused coumarins
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tIn this paper, a series of six dihydropyridine-fused coumarins were synthesized and electrochemicallycharacterized in dimethylformamide (DMF).Dihydropyridine ring oxidation on glassy carbon electrode (GCE) for condensed heterocyclic com-pounds revealed a single anodic peak. Oxidation potential values correlated fairly well with substituenteffects at 9-position. The overall oxidation mechanism involved 2-electrons and 2-protons as determinedby chronoamperometry.Controlled-potential electrolysis followed by UV-Visible spectroscopy proves that dihydropyridine-fused coumarins are electrochemically oxidized in DMF giving rise to the aromatic pyridine derivative.ESR experimental spectra show a triplet, due to the C-centered dihydropyridyl radical trapped withN-tert-butylamine- -phenylnitrone (PBN). Hyperfine coupling constant values (aN) of dihydropyridine-fused coumarins were higher than corresponding values for non-fused ones. These results could be dueto the effect of the coupling of the dihydropyridine moiety with the coumarin ring over the splittingconstant.
Articulo de publicacion SCOPUS
Quote ItemElectrochimica Acta 125 (2014) 457–464