Synthesis and electrochemical oxidation of hybrid compounds:dihydropyridine-fused coumarins
Author
dc.contributor.author
Pardo Jiménez, Viviana Gladys
Author
dc.contributor.author
Barrientos, C.
es_CL
Author
dc.contributor.author
Pérez Cruz, Karina Angélica
es_CL
Author
dc.contributor.author
Navarrete Encina, Patricio
es_CL
Author
dc.contributor.author
Olea Azar, Claudio
es_CL
Author
dc.contributor.author
Núñez Vergara, Luis
es_CL
Author
dc.contributor.author
Squella Serrano, Juan
es_CL
Admission date
dc.date.accessioned
2014-12-15T14:02:01Z
Available date
dc.date.available
2014-12-15T14:02:01Z
Publication date
dc.date.issued
2013
Cita de ítem
dc.identifier.citation
Electrochimica Acta 125 (2014) 457–464
en_US
Identifier
dc.identifier.other
dx.doi.org/10.1016/j.electacta.2014.01.137
Identifier
dc.identifier.uri
https://repositorio.uchile.cl/handle/2250/121899
General note
dc.description
Articulo de publicacion SCOPUS
en_US
Abstract
dc.description.abstract
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.