Electrochemical oxidation of N-substituted 1,4- and 1,2-dihydropyridine derivatives

Stradins, J.; Ogle, John J.; Kadysh, V. P.; Баумане, Л.; Gavars, R.; Дубурс, Г.

doi:10.1016/0022-0728(87)80036-0

Cited by 40 publications

(16 citation statements)

References 20 publications

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“…The shift in the UVabsorption band to the 282 nm region for the N-substituted 1,4-DHP compounds could be due to the pyridinium salt formation [6]. Spectroelectrochemical studies of the resting 1,4-DHP exhibited similar results as shown in Table 1.…”

Section: Spectroelectrochemical Studiessupporting

confidence: 57%

Spectroelectrochemical Study on the Electrooxidation in Aqueous Medium of some 1,4‐Dihydropyridines: Effects of Substitution in 1‐Position and 4‐Position

et al. 2004

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Spectroelectrochemical and HPLC characterization of the electrochemical oxidation in aqueous medium of a series of six N-1 and C-4 substituted 1,4-dihydropyridines is presented. Based on the analysis of spectra obtained by in situ spectroscopic measurements it was possible to detect the generation of final oxidation products, which resulted in differences depending of the nature of the substitution on the nitrogen in the dihydropyridine ring. Controlled potential electrolysis (CPE) in aqueous medium was followed by the HPLC technique using EC and PDA detectors. This latter resulted adequately to follow the parent 1,4-DHP derivatives and their respective oxidation products. Electrochemical oxidation of parent N-H substituted 1,4-dihydropyridines generated the corresponding neutral pyridine derivative as final oxidation product. However, the N-ethyl substituted 1,4-dihydropyridine derivatives gave rise to the pyridinium salt derivatives.

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Section: Spectroelectrochemical Studiessupporting

confidence: 57%

Spectroelectrochemical Study on the Electrooxidation in Aqueous Medium of some 1,4‐Dihydropyridines: Effects of Substitution in 1‐Position and 4‐Position

et al. 2004

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“…Numerous studies have been devoted to the study of the mechanism of oxidation of dihydropyridines of precisely this type. Proposals for the case in question include transfer of hydride ion [3], a one-electron oxidation with subsequent cleavage of a radical [4], and in the majority of cases a two-electron oxidation with cleavage of two protons [5][6][7].…”

mentioning

confidence: 99%

Electrochemical synthesis of 1,2,3,4,4,5,6-substituted 1,4-dihydropyridines

Goba

Turovska

Stradins

et al. 2007

Chem Heterocycl Compd

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It has been shown that chemical oxidation of the methyl ester of 3,4,5-trimethoxycarbonyl-1,2,6-trimethyl-1,4-dihydropyridine to the pyridinium salt, requiring forcing experimental conditions, may be replaced by electrochemical oxidation. On electrochemical reduction of 3,4,5-trimethoxycarbonyl-1,2,6-trimethylpyridinium perchlorate in the presence of alkylating agents 1,2,3,4,4,5,6-substituted 1,4-dihydropyridines are obtained.

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“…The more detailed mechanistic information has been obtained in aprotic media [11][12][13][14][15][16][17][18]. These investigations were generally done by using mainly rotating ring disk electrode (RRDE), linear and cyclic voltammetry and ESR spectroscopy, and have revealed that, in non-aqueous solutions, 1,4-dihydropyridine derivatives are oxidized in a two electron reaction, in particular, in an ECEC mechanism type.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical oxidation of C4-vanillin- and C4-isovanillin-1,4-dihydropyridines in aprotic medium: Reactivity towards free radicals

Salazar

Navarrete-Encina

Camargo

et al. 2008

Journal of Electroanalytical Chemistry

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Electrochemical oxidation of N-substituted 1,4- and 1,2-dihydropyridine derivatives

Cited by 40 publications

References 20 publications

Spectroelectrochemical Study on the Electrooxidation in Aqueous Medium of some 1,4‐Dihydropyridines: Effects of Substitution in 1‐Position and 4‐Position

Spectroelectrochemical Study on the Electrooxidation in Aqueous Medium of some 1,4‐Dihydropyridines: Effects of Substitution in 1‐Position and 4‐Position

Electrochemical synthesis of 1,2,3,4,4,5,6-substituted 1,4-dihydropyridines

Electrochemical oxidation of C4-vanillin- and C4-isovanillin-1,4-dihydropyridines in aprotic medium: Reactivity towards free radicals

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