Electrochemical oxidation of catechol in the presence of cyclopentadiene. Investigation of electrochemically induced Diels–Alder reactions

Nematollahi, Davood; Workentin, Mark S.; Tammari, Esmail

doi:10.1039/b516814g

Cited by 52 publications

(36 citation statements)

References 20 publications

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“…These peaks are correspond to the oxidation of catechol (1a) to o-benzoquinone (2a) and vice versa within a quasi-reversible two electron process. [14][15][16][17][18][19][20][21] The oxidation of catechol (1a) in the presence of 4-mercaptocoumarin (3) as a nucleophile was studied in some details. for a 1 mM solution of 1a in the presence of 1 mM of 4-mercaptocoumarin (3).…”

Section: Resultsmentioning

confidence: 99%

“…1, curve b) that was enhanced during the repetitive recycling of potential is probably due to the formation of a thin film of product at the surface of the electrode, inhibiting, to a certain extent, the performance of the electrode process. [14][15][16][17][18][19][20][21] The overoxidation of 4a was circumvented during the preparative reaction because of the presence of the electron-withdrawing group.…”

Section: Resultsmentioning

confidence: 99%

“…[14][15][16][17][18][19][20][21] All chemicals were reagent-grade materials. Sodium acetate, solvents and reagents were of pro-analysis.…”

Section: Methodsmentioning

confidence: 99%

“…12,13) A literature survey reveals that, in contrast to the widely studied, coumarin derivatives, no paper has reported the synthesis of 4-(dihydroxyphenylthio)-2H-chromen-2-one derivatives. Following our experiences in electrochemical oxidation of catechols in the presence of nucleophiles, [14][15][16][17][18][19][20][21] we envisaged that synthesis of organic compounds with both structures of catechol and coumarin might cause an enhancement of pharmaceutical properties and medicinal activities. This idea prompted us to investigate the electrochemical oxidation of catechols in the presence of 4-mercaptocoumarin as the nucleophile and we have discovered an easy and one-pot electrochemical method for the synthesis of 4-(dihydroxyphenylthio)-2H-chromen-2-one derivatives (4a-d) in high yield and purity, using this environmentally friendly method with high atom economy.…”

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Electrochemical Synthesis of 4-(Dihydroxyphenylthio)-2H-chromen-2-one Derivatives

Nematollahi

Azizian

Sargordan-Arani

et al. 2008

CHEMICAL & PHARMACEUTICAL BULLETIN

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The number of natural and synthetic coumarin (2H-chromen-2-one) derivatives 1) have been reported to exert notably antimicrobial 2,3) as well as antifungal, 4,5) tuberculostatic 6) and anti-human immunodeficiency virus (HIV) 7,8) activity. Moreover, the antibiotic novobiocin belongs to the hydroxycoumarin series. The importance of these compounds have motivated many workers to synthesize a number of them, and numerous methods have been developed for their preparation.9-11) On the other hand, catechols are a promising group of compounds worthwhile for further investigation, which may lead to the discovery of selective acting, biodegradable agrochemicals having high human, animal and plant compatibility. 12,13) A literature survey reveals that, in contrast to the widely studied, coumarin derivatives, no paper has reported the synthesis of 4-(dihydroxyphenylthio)-2H-chromen-2-one derivatives. Following our experiences in electrochemical oxidation of catechols in the presence of nucleophiles, [14][15][16][17][18][19][20][21] we envisaged that synthesis of organic compounds with both structures of catechol and coumarin might cause an enhancement of pharmaceutical properties and medicinal activities. This idea prompted us to investigate the electrochemical oxidation of catechols in the presence of 4-mercaptocoumarin as the nucleophile and we have discovered an easy and one-pot electrochemical method for the synthesis of 4-(dihydroxyphenylthio)-2H-chromen-2-one derivatives (4a-d) in high yield and purity, using this environmentally friendly method with high atom economy. In order to study the feasibility of the electrochemical synthesis of 4-(dihydroxyphenylthio)-2H-chromen-2-one derivatives (4a-d) and mechanistic aspects of this conversions, electrochemical oxidation of catechols in the absence and presence of 4-mercaptocoumarin was studied using cyclic voltammetry. As well, in this work computational studies were used for quantitative answer to the question concerning the difference in electrochemical oxidation of catechol in the presence of 4-hydroxycoumarin and 4-mercaptocoumarin. Results and DiscussionElectrochemical Studies Figure 1, curve a, shows the voltammetric curve obtained for the oxidation of catechol (1 mM) in water/acetonitrile (50/50) solution containing sodium acetate (cϭ0.2 M) on a glassy carbon electrode. In the studied potential-range, a well defined voltammetric curve is obtained that has an anodic (A 1 ) and the corresponding cathodic (C 1 ) peaks. These peaks are correspond to the oxidation of catechol (1a) to o-benzoquinone (2a) and vice versa within a quasi-reversible two electron process.14-21) The oxidation of catechol (1a) in the presence of 4-mercaptocoumarin (3) as a nucleophile was studied in some details. The 4-(dihydroxyphenylthio)-2H-chromen-2-one derivatives have been synthesized by direct electrochemical oxidation of catechols in the presence of 4-mercaptocoumarin as a nucleophile in water/acetonitrile (50/50) solution, in a one-pot process, at carbon rod electrode, in an undivided...

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

“…[14][15][16][17][18][19][20][21] All chemicals were reagent-grade materials. Sodium acetate, solvents and reagents were of pro-analysis.…”

Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

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Electrochemical Synthesis of 4-(Dihydroxyphenylthio)-2H-chromen-2-one Derivatives

Nematollahi

Azizian

Sargordan-Arani

et al. 2008

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…The selected criterion for simulation progress was achieving to the best fitting between simulated and experimental linear sweep voltammograms [19]. This work was performed by data fitting function of DigiElch simulation software [12].…”

Section: Kinetics Evaluation Of Chemical Stepmentioning

confidence: 99%

Kinetics and Mechanistic Study of Acetaminophen‐Captopril Interaction by Electrochemical Methods

Tammari

Nematollahi

2011

Electroanalysis

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In this work kinetics parameters and electrochemical mechanism for electrooxidation of acetaminophen in the absence and presence of captopril in a condition close to acetaminophen natural oxidation pathway was investigated. The electrooxidation of acetaminophen in the presence of captopril was investigated by voltammetry and coulometry methods. The results of this work show that acetaminophen is oxidized to its respective p-quinoneimine. The quinoneimine attacked by captopril, forms thioether. The proposed electrochemical mechanism is ECEC. The estimated value for homogeneous rate constant k obs is 3.1 10 4 AE 155 M

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Modified electrodes: Utilizing Cu‐modified graphene oxide nanosheets as a cathode in electro‐oxidation synthesis of mild Suzuki–Miyaura cross‐coupling reaction under green and sustainable conditions

Abdullaev,

Singh,

Al‐Delfi

et al. 2024

Applied Organom Chemis

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This study presents an eco‐conscious approach to enhance the efficiency of the Suzuki–Miyaura cross‐coupling reaction. We first synthesized graphene oxide nanosheets using the Hummers method and then coated them to incorporate metallic copper on their surface. Following this, we conducted various analyses, including Fourier transform infrared spectroscopy (FT‐IR), scanning electron microscopy (SEM), transmission electron microscopy (TEM), Brunauer–Emmett–Teller (BET) analysis, cyclic voltammetry (CV), and energy‐dispersive X‐ray spectroscopy (EDS) identification, to characterize these modified nanosheets. Subsequently, we utilized Cu‐modified graphene oxide nanosheets as cathode catalysts in an electro‐oxidation synthesis setup. To verify the effectiveness of this novel approach, we utilized bromobenzene and phenylboronic acid as model substrates to synthesize biphenyl compounds. The reaction yielded impressive product yields ranging from 87% to 93%. Operating under environmentally friendly conditions, this electro‐oxidation synthesis not only enhances selectivity but also significantly reduces the environmental impact of the reaction. Our findings highlight the potential of this green chemistry strategy, offering a promising avenue for sustainable and efficient organic synthesis, as evidenced by the successful coupling of bromobenzene and phenylboronic acid with consistently high yields.

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Electrochemical oxidation of catechol in the presence of cyclopentadiene. Investigation of electrochemically induced Diels–Alder reactions

Abstract: We describe the synthesis and kinetic evaluation of compounds from [4 + 2] alone and [4 + 2] followed by [2 + 2] cycloaddition reactions of electrochemically generated o-benzoquinone with 1,3-cyclopentadiene.

Cited by 52 publications

References 20 publications

Electrochemical Synthesis of 4-(Dihydroxyphenylthio)-2H-chromen-2-one Derivatives

Electrochemical Synthesis of 4-(Dihydroxyphenylthio)-2H-chromen-2-one Derivatives

Kinetics and Mechanistic Study of Acetaminophen‐Captopril Interaction by Electrochemical Methods

Modified electrodes: Utilizing Cu‐modified graphene oxide nanosheets as a cathode in electro‐oxidation synthesis of mild Suzuki–Miyaura cross‐coupling reaction under green and sustainable conditions

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