Voltammetric oxidation of Hantzsch 1,4-dihydropyridines in protic media: substituent effect on positions 3,4,5 of the heterocyclic ring

Arguello, J; Nunez-Vergara, LJ; Sturm, JC; Squella, JA

Abstract

A detailed study was done of the electrochemical oxidation of some 1,4-dihydropyridine (1,4-DHP) derivatives in order to determine the influence of the substituents in the heterocyclic ring. Two types of derivatives were synthesized, namely, 3,5-(substituted)-4-(5?-nitro-2?-furyl)-1,4-DHP for series A, and 3,5-dicarboethoxy-4-(substituted or non-substituted)-1,4-DHP for series B. Voltammetry, coulometry, controlled potential electrolysis, UV-vis spectroscopy and GC-MS techniques were employed to collect data that permitted to postulate oxidation mechanisms in a protic medium. In acid media, at pH < 4, all derivatives follow oxidation mechanisms obeying the ECE sequence. However, at pH > 4, series A derivatives follow an ECEC sequence, while series B derivatives obey a DISP1 mechanism. In both cases, the uptake of proton at N-l by the OH- ion of the media was the rate-determining step. © 2004 Elsevier Ltd. All rights reserved.

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Título según WOS: Voltammetric oxidation of Hantzsch 1,4-dihydropyridines in protic media: substituent effect on positions 3,4,5 of the heterocyclic ring
Título según SCOPUS: Voltammetric oxidation of Hantzsch 1,4-dihydropyridines in protic media: Substituent effect on positions 3,4,5 of the heterocyclic ring
Título de la Revista: ELECTROCHIMICA ACTA
Volumen: 49
Número: 27
Editorial: PERGAMON-ELSEVIER SCIENCE LTD
Fecha de publicación: 2004
Página de inicio: 4849
Página final: 4856
Idioma: English
URL: http://linkinghub.elsevier.com/retrieve/pii/S0013468604005651
DOI:

10.1016/j.electacta.2004.05.037

Notas: ISI, SCOPUS