Electrochemical Studies of Newly Synthesized 1,4-Dihydropyridine-Based Hexahydroquinoline Derivatives

Tavakkoli, Zahra; Goljani, Hamed; Gündüz, Miyase Gözde; Tahir, Muhammad Nawaz; Nematollahi, Davood

doi:10.1149/1945-7111/abaa6c

Cited by 7 publications

(2 citation statements)

References 25 publications

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“…It should be noted that we confirmed the single-electron transfer of the PPF oxidation process using the half-peak width of the differential pulse voltammogram of an irreversible electrochemical reaction. 21 The first and second cyclic voltamograms of PPF (1.0 mM) in water (phosphate buffer, pH 2.0, c = 0.2 M)/acetonitrile (50/50 v/v) mixture are shown in Fig. 2.…”

Section: Resultsmentioning

confidence: 99%

Electrochemical Study of Propofol (2,6-diisopropylphenol): A Novel Insight into the Dimerization of Propofol

Mohamadighader

Nematollahi

Saraei

2021

J. Electrochem. Soc.

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Electrochemical oxidation of propofol (2,6-diisopropylphenol) (PPF) has been studied in a water/acetonitrile (50/50, v/v) mixture by cyclic voltammetry, differential pulse voltammetry and galvanostatic coulometry. The results show that PPF can be electrochemically oxidized in a chemically irreversible one-electron/one-proton process to form the corresponding radical (PPF • ) which couples to yield propofol dimer (PD). Due to the easier oxidation of PD compared to PPF, the PD is oxidized in a reversible two-electron/two-proton process to form 3,3′,5,5′-tetraisopropyl-[1,1′-bi(cyclohexylidene)]-2,2′,5,5′-tetraene-4,4′-dione (PDQ). We call this mechanism EDE for simplicity, where E represents an electron transfer at an electrode surface and D represents a homogeneous dimerization step. We also investigated the catalytic effect of sulfite ions on the oxidation of PPF and found strong evidence to support it. The electrochemical synthesis of PDQ was successfully carried out directly using drug samples or by using commercial samples of PPF in the presence of sodium sulfite as a catalyst. The electrochemical dimerization of PPF is carried out under mild conditions at room temperature and atmospheric pressure in an undivided cell using carbon anode and stainless steel cathode, using the electrode as an electron source instead of toxic oxidants, under greener conditions.

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Section: Resultsmentioning

confidence: 99%

Electrochemical Study of Propofol (2,6-diisopropylphenol): A Novel Insight into the Dimerization of Propofol

Mohamadighader

Nematollahi

Saraei

2021

J. Electrochem. Soc.

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“…The oxidation process (heteroaromatization) of the 1,4-dihydropyridine, 1,4-dihydropyrimidine and azolo-1,4dihydropyrimidine derivatives was studied by both experimental [18][19][20][21][22] and theoretical [23][24][25] methods. It turned out that this process leads mainly to heteroaromatization of the partially hydrogenated cycle.…”

Section: Introductionmentioning

confidence: 99%

Oxidation process of 1,4-dihydropyridine, 1,4-dihydropyrimidine, and pyrrolo-1,4-dihydropyrimidine: quantum chemical study

Shyshkina,

Desenko

2024

Struct Chem

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Derivatives of 1,4-dihydropyridine, 1,4-dihydropyrimidine and its azolo analogues possess a wide range of biological activity and are involved in cellular bioenergetics. Dihydrocycles can be oxidized up to corresponding aromatic ones due to two one-electron transfers. Mechanism of the oxidation process was modeled as a stepwise change of the 1,4-dihydropyridine, 1,4-dihydropyrimidine and pyrrolo-1,4-dihydropyrimidine using different levels of theory (Hartree-Fock, MP2, DFT), basis sets, and models of environment (vacuum approximation, PCM model describing a non-speci c in uence of polarizing environment, or PCM model with an explicit water molecule describing both non-speci c and speci c in uence of neighboring molecules). It is shown that the potential of the rst one-electron transfer I 1 depends on the level of theory and the model of an environment used in calculations.The potential of the second one-electron transfer I 2 depends only on the model of an environment. The analysis of their differences calculated using different approaches has revealed the dependence only from the level of theory.Since DFT methods provide the geometric characteristics of 1,4-dihydroheterocycles closest to the experimental data, it seems reasonable to use these relatively cheap calculations to study the oxidation process.

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Expanding cyclodextrin use in normal phase and super/subcritical fluid chromatographic modes for the chiral separation of 1,4-dihydropyridines

Burk,

Sajeevan J,

Salehi

et al. 2024

Journal of Chromatography A

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Electrochemical Studies of Newly Synthesized 1,4-Dihydropyridine-Based Hexahydroquinoline Derivatives

Cited by 7 publications

References 25 publications

Electrochemical Study of Propofol (2,6-diisopropylphenol): A Novel Insight into the Dimerization of Propofol

Electrochemical Study of Propofol (2,6-diisopropylphenol): A Novel Insight into the Dimerization of Propofol

Oxidation process of 1,4-dihydropyridine, 1,4-dihydropyrimidine, and pyrrolo-1,4-dihydropyrimidine: quantum chemical study

Expanding cyclodextrin use in normal phase and super/subcritical fluid chromatographic modes for the chiral separation of 1,4-dihydropyridines

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