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

Abstract

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.

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

“…In 2017, Nematollahi and co‐workers reported the synthesis of sulfonyl derivatives of p ‐methylaminophenol through the reaction of electrogenerated p ‐methylquinoneimine with sulfinic acids. Some mono‐ and bis(or tris)sulfonyl‐ p ‐(methylamino)phenol derivatives were obtained by changing the applied potential (Scheme ) . This method does not deal with organic solvents and strong acid/bases.…”

Interfacial Proton Supply/Filtration Regulates the Dynamics of Electrocatalytic Nitrogen Reduction Reaction: A Perspective

“…[ 53–56 ] 3)The design of the experimental apparatus is also the key to facilitate the electrochemical eNRR system. [ 57 ] Different structures of electrolytic cells [ 58 ] and electrodes have different effects and regulations on the convection field, which in turn will affect the transmission of protons in the electrolyte, the supply of reactant nitrogen, and the diffusion of product ammonia. [ 15,59,60 ] This is despite considerable efforts and significant improvements in yields and Faraday efficiency, in the catalyst itself creation, electrolyte exploration, and device design is still in the early stage, and there are still some problems to be discussed.…”

Electrochemical study of 4-chloroaniline in a water/acetonitrile mixture. A new method for the synthesis of 4-chloro-2-(phenylsulfonyl)aniline and N-(4-chlorophenyl)benzenesulfonamide

“…29,30 In addition, diaryl sulfones were synthesized by Nicatalysed photoredox sulnylation of halides, 31 cross coupling of aryl iodide with sulnate salts in the presence of photoredox/ Ni catalyst, 32 Cu-catalyzed direct sulfonylation of indolines, 33 silver-promoted decarboxylative sulfonylation of aromatic carboxylic acids with sodium sulnates, 34 arenes and 3CdSO 4 -$xH 2 O in the presence of P 2 O 5 via mechanochemistry 35 and electrochemical methods. [36][37][38] All of these methods are efficient in synthesis of diaryl sulfones. They all have strengths, capabilities and weaknesses.…”