Electrochemical Synthesis of Sulfonamide Derivatives Based on the Oxidation of 2,5-Diethoxy-4-Morpholinoaniline in the Presence of Arylsulfinic Acids

Beiginejad, Hadi; Nematollahi, Davood

doi:10.1021/jo500812d

Cited by 21 publications

(21 citation statements)

References 17 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…All of these results are in agreement with the participation of electrogenerated MQI in the Michael addition reaction with BS [28][29][30][31][32][33][34] . Fig.…”

Section: Resultssupporting

confidence: 82%

A green strategy for the synthesis of sulfone derivatives of p-methylaminophenol: Kinetic evaluation and antibacterial susceptibility

Nematollahi

Khazalpour

Ranjbar

et al. 2017

Sci Rep

Self Cite

View full text Add to dashboard Cite

This is one of the few examples in which the diverse products have been synthesized just by changing the applied potential. The synthesis of sulfonyl derivatives of p-methylaminophenol were carried out by reaction of the electrogenerated p-methylquinoneimine with sulfinic acids. Various types of mono (MSP), bis (BSP) and tris (TSP) sulfonyl p-methyl aminophenols were obtained by changing the electrode potential, in one pot under green conditions. The mono sulfonyl-p-(methylamino)phenol derivatives (MSP) were assessed for their in vitro antibacterial activity against the gram positive (Staphylococcus aureus) and gram negative (Escherichia coli) strains. It was found that the tested compounds were more active against Staphylococcus aureus than Escherichia coli. We also found that the antimicrobial activity of MSP derivatives to vary in the order MSP4 (R = CH3) > MSP1 (R = p-tolyl) ≈ MSP2 (R = phenyl) > MSP3 (R = p-ClC6H4). Moreover, the observed homogeneous rate constants (k obs) of the reaction of p-methyl quinoneimine with sulfinic acids were estimated in various pH values, based on the EC and ECEC mechanisms, by comparing the simulated cyclic voltammograms with the experimental ones.

show abstract

“…All of these results are in agreement with the participation of electrogenerated MQI in the Michael addition reaction with BS [28][29][30][31][32][33][34] . Fig.…”

Section: Resultssupporting

confidence: 82%

A green strategy for the synthesis of sulfone derivatives of p-methylaminophenol: Kinetic evaluation and antibacterial susceptibility

Nematollahi

Khazalpour

Ranjbar

et al. 2017

Sci Rep

Self Cite

View full text Add to dashboard Cite

show abstract

“…Increasing substrate concentration causes the peak current ratio (I pC1 /I pA1 ) to decrease proportionally. Using previous works on the electrochemical oxidation of 2,5-DEMA [26,27] and the present data, it can be said that the cathodic peak C 0 is related to the electrochemical reduction of the product which is produced after trimerization reaction.…”

Section: Resultssupporting

confidence: 57%

“…Investigations indicated that dimerization, trimerization, hydrolysis, and hydroxylation can occur in electrochemical oxidation of amines which is highly dependent on pH of solution [24,25]. Along with our previous works in electrochemical study of amines [23][24][25][26][27][28], diversity of behavior in the electrochemical oxidation of 2,5-diethoxy-4-morpholinoaniline (2,5-DEMA, 1) at various conditions and also the importance of Schiff base reaction [29] prompted us to studying electrochemical oxidation of 2,5-DEMA at various conditions using cyclic voltammetry (CV) and controlled-potential coulometry. The results show that in all pHs electrochemically generated p-quinonediimine (1ox ?…”

Section: Introductionmentioning

confidence: 53%

“…in the timescale of our experiments is unstable and participates in following chemical reactions. Previous works show that in this condition the hydrolysis is a chemical following reaction and the cathodic peak C 2 relates to the electrochemical reduction of the product which is produced after hydrolysis reaction [26,27].…”

Section: Resultsmentioning

confidence: 98%

“…Our experiences on electrochemical oxidation of amines at various conditions [24][25][26][27][28], diagnostic criteria of cyclic voltammetry and controlled-potential coulometry (Figs. 6,7,8,9), consumption of two electrons per molecule of 1 and the mass spectrum of isolated product (m/z = 551) allow us to propose ECEC pathway for the electrochemical oxidation of 2,5-DEMA (1) in strongly alkaline pHs (Scheme 2).…”

Section: Resultsmentioning

confidence: 99%

See 2 more Smart Citations

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

Beiginejad

Nematollahi

2015

Monatsh Chem

Self Cite

View full text Add to dashboard Cite

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

show abstract

Electrochemical Synthesis of Sulfonamide Derivatives: Electrosynthesis Conditions and Reaction Pathways

Talebi,

Nematollahi

2024

ChemElectroChem

Self Cite

View full text Add to dashboard Cite

In 2014, the World Health Organization called drug resistance to antibiotics a “major global threat”. Therefore, the ever‐increasing human need for new antibiotics with greater effectiveness and fewer side effects is a necessity. Meanwhile, sulfonamides are among the most widely used antibiotics in the world. In this review, attention has been paid to the key points raised in various papers in the field of electrosynthesis of these compounds, considering their positive and negative aspects, including interaction as much as possible with the principles of green chemistry and the absence of environmental risks, low cost and the versatility and scalability of the method used along with acceptable efficiency. In the following, we will discuss research focused on the synthesis of sulfonamide derivatives based on the oxidation or reduction of various compounds which take place on the working electrode surface.

show abstract

Electrochemical Synthesis of Sulfonamide Derivatives Based on the Oxidation of 2,5-Diethoxy-4-Morpholinoaniline in the Presence of Arylsulfinic Acids

Cited by 21 publications

References 17 publications

A green strategy for the synthesis of sulfone derivatives of p-methylaminophenol: Kinetic evaluation and antibacterial susceptibility

A green strategy for the synthesis of sulfone derivatives of p-methylaminophenol: Kinetic evaluation and antibacterial susceptibility

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

Electrochemical Synthesis of Sulfonamide Derivatives: Electrosynthesis Conditions and Reaction Pathways

Contact Info

Product

Resources

About