Electrochemical oxidation of some dihydroxybenzene derivatives in the presence of indole

Nematollahi, Davood; Dehdashtian, Sara; Ниази, Али

doi:10.1016/j.jelechem.2008.01.012

Cited by 59 publications

(40 citation statements)

References 33 publications

(38 reference statements)

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“…These observations make it possible for us to propose the pathway in Scheme 2 for the electrooxidation of 3,4-dihydroxybenzoic acid (2) in the presence of triphenylphosphine (4). Furthermore, for high scan rates as well as acidic solutions [19,20], only peak C 1 is observed and the other cathodic peak (C 0 ) disappears. Under these conditions, the voltammogram shows a quasi-reversible two-electron process corresponding to a 2,5-dihydroxybenzoic acid (3)/3,6-dioxocyclohexa-1,4-dienecarboxylic acid (3a) redox couple [19][20][21].…”

Section: Electrochemical Study Of 34-dihydroxybenzoic Acid (2)mentioning

confidence: 93%

“…Furthermore, for high scan rates as well as acidic solutions [19,20], only peak C 1 is observed and the other cathodic peak (C 0 ) disappears. Under these conditions, the voltammogram shows a quasi-reversible two-electron process corresponding to a 2,5-dihydroxybenzoic acid (3)/3,6-dioxocyclohexa-1,4-dienecarboxylic acid (3a) redox couple [19][20][21]. Such a situation is indicative of a coupled chemical reaction such as hydroxylation following the abstraction of two electrons from 2,5-dihydroxybenzoic acid (3) and is observed when the time scale of the experiment and the half-life of the chemical reaction are comparable [22,23].…”

Section: Electrochemical Study Of 34-dihydroxybenzoic Acid (2)mentioning

confidence: 93%

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Kinetics study of electrochemically induced michael reaction of benzoquinones with triphenylphosphine

Nematollahi

Esmaili

2010

JICS

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The electrochemical oxidation of 3,4-dihydroxybenzaldehyde (1), 3,4-dihydroxybenzoic acid (2) and 2,5-dihydroxybenzoic acid (3) were studied in the presence of triphenylphosphine (4) as a nucleophile using cyclic voltammetry and controlled-potential coulometry. The results indicate that the quinones derived from oxidation of 3,4-dihydroxybenzaldehyde, 3,4-dihydroxybenzoic acid and 2,5-dihydroxybenzoic acid participate in Michael addition reaction with triphenylphosphine (4). In this work, based on an EC mechanism, the observed homogeneous rate constants (k obs ) of the reaction of produced benzoquinones with triphenylphosphine (4) were estimated by comparing the experimental cyclic voltammograms with the digitally simulated results.

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Section: Electrochemical Study Of 34-dihydroxybenzoic Acid (2)mentioning

confidence: 93%

Section: Electrochemical Study Of 34-dihydroxybenzoic Acid (2)mentioning

confidence: 93%

Kinetics study of electrochemically induced michael reaction of benzoquinones with triphenylphosphine

Nematollahi

Esmaili

2010

JICS

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“…1, curve a). [2][3][4][5][6][7][8][9][10][11] The electrooxidation of catechol (1a) in the presence of phenyl-Meldrum's acid (3) was studied in some detail. Fig.…”

Section: Resultsmentioning

confidence: 99%

“…Many flavonoids and catechol derivatives turned out to be as antimicrobial agents. 1) In this connection, in order to synthesis catechol derivatives, we studied the electrochemical oxidation of benzenediols in the presence of CH acid nucleophiles, [2][3][4] SH acid nucleophiles, [5][6][7][8][9] nitrite ion 10) and triphenylphosphine. 11) Also, it is demonstrated that, in comparison with simple catechols, the "highly oxygenated compounds with catechol ring" exhibit interesting biological activities.…”

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confidence: 99%

Electrochemical Oxidation of Catechols in the Presence of Phenyl-Meldrum's Acid. Synthesis and Kinetic Evaluation

Nematollahi

Bamzadeh

Shayani‐Jam

2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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23Catechol, by itself, and mono-substituted catechols are active in part against Pseudomonas, Bacillus, but not Penicillium species. Many flavonoids and catechol derivatives turned out to be as antimicrobial agents. 1) In this connection, in order to synthesis catechol derivatives, we studied the electrochemical oxidation of benzenediols in the presence of CH acid nucleophiles, 2-4) SH acid nucleophiles, 5-9) nitrite ion 10) and triphenylphosphine. 11) Also, it is demonstrated that, in comparison with simple catechols, the "highly oxygenated compounds with catechol ring" exhibit interesting biological activities.12,13) Therefore, the development of a simple synthetic route for the synthesis of "highly oxygenated compounds with catechol ring" from readily available reagents is one of the major tasks. In this direction, we recently reported the synthesis of some "highly oxygenated compounds with catechol ring." 14) This idea prompted us to investigate the electrochemical oxidation of catechols in the presence of phenyl-Meldrum's acid as a nucleophile and represents a facile and one-pot electrochemical method for the synthesis of some new "highly oxygenated compounds with catechol ring." Also, an additional purpose of this work is the kinetic and mechanistic study of the electrochemical oxidation of catechols in the presence of phenyl-Meldrum's acid and the estimation of the observed homogeneous rate constants (k obs ) of reaction of electrochemically generated o-benzoquinones with this nucleophile by digital simulation of cyclic voltammograms. Results and DiscussionElectrochemical Investigations The cyclic voltammogram of 1.0 mM catechol (1a) in aqueous solution containing 0.2 M acetate buffer (pHϭ5.0) shows one anodic peak (A 1 ) and the corresponding cathodic peak which correspond to the transformation of catechol (1a) to o-benzoquinone (2a) and vice-versa, within a quasi-reversible two electron process (Fig. 1, curve a).2-11) The electrooxidation of catechol (1a) in the presence of phenyl-Meldrum's acid (3) was studied in some detail. Fig. 1, curve b, shows the first cyclic voltammogram obtained for a 1.0 mM solution of 1a in the presence of 0.1 mM phenyl-Meldrum's acid (3). The voltammogram exhibits one anodic peak (A 1 ) and one cathodic peak (C 1 ) that shows decreasing in comparison to the cathodic peak of catechol (1a) in the absence of 3. In this figure, curve c is the voltammogram of 3 in the absence of 1a.The effect of potential sweep rate on shape of cyclic voltammograms of catechol (1a) in the presence of phenylMeldrum's acid (3) was studied, too. It is seen that, proportional to the augmentation of the potential sweep rate, the height of peak C 1 increases. A similar situation is observed when the 3 to 1a concentration ratio is decreased. A plot of the peak current ratio (I pC1 /I pA1 ) versus the scan rate for a mixture of catechol (1a) and phenyl-Meldrum's acid (3) confirms the reactivity of o-benzoquinone (2a) toward phenylMeldrum's acid (3), appearing as an increase in the peak cur- Electrochemic...

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“…In these procedures, cleanly generated electricity acts as a ''green'' catalyst. Among electrochemical synthesis of various organic compounds reported in the literature [31][32][33][34][35][36], few are dependent on electro-catalytic multi-component condensations [37][38][39].…”

Section: Introductionmentioning

confidence: 99%

A domino electro-oxidative synthesis of 3,3′-bis(indolyl)methane nanoparticles

Nikoofar

Ghanbari

2015

Monatsh Chem

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An effective route for electro-oxidative synthesis of 3,3 0 -bis(indolyl)methane nanoparticles has been described via a domino multi-component reaction between various alcohols and indole derivatives in an undivided cell under constant potential conditions in CH 3 CN at room temperature. The mechanistic aspect of this electro-oxidative condensation has also been studied by UV-Vis spectra and cyclic voltammograms. The nanostructure of the products has been confirmed by scanning electron microscopy. Graphical abstract N H N -OH O --2e + ,-2H -+1e N H N H Carbon anode Carbon cathod

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Electrochemical oxidation of some dihydroxybenzene derivatives in the presence of indole

Cited by 59 publications

References 33 publications

Kinetics study of electrochemically induced michael reaction of benzoquinones with triphenylphosphine

Kinetics study of electrochemically induced michael reaction of benzoquinones with triphenylphosphine

Electrochemical Oxidation of Catechols in the Presence of Phenyl-Meldrum's Acid. Synthesis and Kinetic Evaluation

A domino electro-oxidative synthesis of 3,3′-bis(indolyl)methane nanoparticles

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