Electrochemical oxidation of 4-substituted urazoles in the presence of arylsulfinic acids: an efficient method for the synthesis of new sulfonamide derivatives

Varmaghani, Fahimeh; Nematollahi, Davood; Mallakpour, Shadpour; Esmaili, Roya

doi:10.1039/c2gc16342j

Cited by 53 publications

(39 citation statements)

References 21 publications

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“…1 in low scan rate (100 mV/s), the cyclic voltammogram exibits the feature of an irreversible electron-transfer process with an anodic peak (A 1 ) at 0.70 V vesus Ag/AgCl which corresponds to the transformation of 4-phenylurazole (1) to 4-phenyl-4H-1,2,4-triazole-3,5-dione (1ox) (Scheme 1). 25 It is seen that, proportionally to the augmentation of potential sweep rate, the peak current ratio (I pC1 /I pA1 ) increases. The ratio of I pC1 /I pA1 and the anodic peak current function, I pA1 /v 1/2 , versus the potential scan rate are also shown in Fig.…”

Section: Resultsmentioning

confidence: 94%

Oxidative Ring Cleavage of 4-(4-R-phenyl)-1,2,4-triazolidine-3,5-diones: Electrochemical Behavior and Kinetic Study

Varmaghani

Nematollahi

Mallakpour

2012

J. Electrochem. Soc.

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Cyclic voltammetry results as a diagnostic technique for electrochemical oxidation of 4-(4-R-phenyl)-1,2,4-triazolidine-3,5-diones (1-5) are reported and discussed. The results indicate that the electrochemically generated 4-(4-R-phenyl)-4H-1,2,4-triazole-3,5-diones (1ox-5ox) are unstable and participate in oxidative ring cleavage. In this study, the effect of different parameters such as pH, 4-phenylurazole concentration, solvent, temperature, substitute effect and time window of chosen electrochemical method have been studied. Also, the transfer coefficient, α, exchange current density, J 0 , the formal potential, E 0' and diffusion coefficient, D, of 4-phenylurazole (1) have been calculated. In addition, the observed homogeneous rate constants of oxidative ring cleavage of 4-phenylurazole derivatives were estimated by comparing the experimental cyclic voltammetric responses with digital simulated results.

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Section: Resultsmentioning

confidence: 94%

Oxidative Ring Cleavage of 4-(4-R-phenyl)-1,2,4-triazolidine-3,5-diones: Electrochemical Behavior and Kinetic Study

Varmaghani

Nematollahi

Mallakpour

2012

J. Electrochem. Soc.

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“…Electrochemical oxidation of 2,5-DEMA (1) at various pHs shows that the electrode surface reaction at pH [ 5.23, corresponds to the two-electron, one-proton process (Scheme 1) [26]. Electrochemical oxidation of various species in the presence different nucleophiles indicates that the peak current ratio (I pC /I pA ) decreases upon increasing power nucleophilicity of nucleophiles [31,32]. In other words, in pH upper than 5.23, 1H ?…”

Section: Resultsmentioning

confidence: 99%

Mechanistic study of electrochemical oxidation of 2,5-diethoxy-4-morpholinoaniline in aqueous solutions: hydrolysis, trimerization, and hydroxylation processes

Beiginejad

Nematollahi

2015

Monatsh Chem

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The electrochemical oxidation of 2,5-diethoxy-4-morpholinoaniline has been studied in various pHs using cyclic voltammetry and controlled potential coulometry.The results indicate that the electrochemically generated pquinonediimine participates in different types of reactions (hydrolysis, hydroxylation, and trimerization). Instability of the produced p-quinonediimine depends on its structure, higher nucleophilicity of 2,5-diethoxy-4-morpholinoaniline, and pH of solution. In lower pH range, rate of hydrolysis is faster than hydroxylation and dimerization. In intermediate pHs rate of the dimerization is faster than hydrolysis and hydroxylation, and in the strongly alkaline solution, rate of the hydroxylation is faster than hydrolysis and dimerization. The effect of the charge of reaction site (C 1 ) and N 1 =C 1 bond order (Wiberg bond indices) on the hydrolysis rate were studied. Calculations were performed using density functional theory B3LYP level of theory and 6-311?G(p,d) basis set. Graphical abstract NH2 N O OEt EtO -2e--H+ n o b r a C e d o n A HN N O EtO OEt O OEt EtO O NH N O EtO OEt NH2 N O OEt EtO NH N O OEt EtO HO pH =1 0-13 pH =5. 3-9 -2e-EtO O O pH=1-3 -2H+ NH3 NH O OEt EtO NH2 N O OEt EtO NH N O OEt EtO HN N O EtO OEt O OEt EtO O NH N O EtO OEt NH2 NH O OEt EtO -2e--2H+ pH=4-5.2 NH N O OEt EtO OEt

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“…In 2012, Nematollahi and co‐workers reported the electrochemical synthesis of some sulfonamide derivatives through the electro‐oxidation of 4‐propyl and 4‐butyl derivatives of urazole in the presence of arylsulfinic acids as nucleophiles (Scheme ) . It is proposed that electrogenerated 4‐alkyl‐4 H ‐1,2,4‐triazole‐3,5‐diones are attacked by arylsulfinic acids.…”

Section: C−s Bond Formation or S−x (X=n O S Se) Bond Formation Thrmentioning

confidence: 99%

Electrocatalytic Oxidative Transformation of Organic Acids for Carbon–Heteroatom and Sulfur–Heteroatom Bond Formation

Hong

Xiao

et al. 2020

ChemSusChem

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The electrolysis of organic acids has garnered increasing attention in recent years. In addition to the famous electrochemical decarboxylation known as Kolbe electrolysis, a number of other electrochemical processes have been recently established that allow for the construction of carbon–heteroatom and sulfur–heteroatom bonds from organic acids. Herein, recent advances in electrochemical C−X and S−X (X=N, O, S, Se) bond‐forming reactions from five classes of organic acids and their conjugate bases, namely, carboxylic, thiocarboxylic, phosphonic, sulfinic, and sulfonic acids, are surveyed.

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Electrochemical oxidation of 4-substituted urazoles in the presence of arylsulfinic acids: an efficient method for the synthesis of new sulfonamide derivatives

Cited by 53 publications

References 21 publications

Oxidative Ring Cleavage of 4-(4-R-phenyl)-1,2,4-triazolidine-3,5-diones: Electrochemical Behavior and Kinetic Study

Oxidative Ring Cleavage of 4-(4-R-phenyl)-1,2,4-triazolidine-3,5-diones: Electrochemical Behavior and Kinetic Study

Mechanistic study of electrochemical oxidation of 2,5-diethoxy-4-morpholinoaniline in aqueous solutions: hydrolysis, trimerization, and hydroxylation processes

Electrocatalytic Oxidative Transformation of Organic Acids for Carbon–Heteroatom and Sulfur–Heteroatom Bond Formation

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