7463-22-1Relevant articles and documents
A facile and versatile electro-reductive system for hydrodefunctionalization under ambient conditions
Huang, Binbin,Guo, Lin,Xia, Wujiong
supporting information, p. 2095 - 2103 (2021/03/26)
A general electrochemical system for reductive hydrodefunctionalization is described, employing the inexpensive and easily available triethylamine (Et3N) as a sacrificial reductant. This protocol is characterized by facile operation, sustainable conditions, and exceptionally wide substrate scope covering the cleavage of C-halogen, N-S, N-C, O-S, O-C, C-C and C-N bonds. Notably, the selectivity and capability of reduction can be conveniently switched by simple incorporation or removal of an alcohol as a co-solvent.
Potassium tert-butoxide-mediated metal-free synthesis of sulfonamides from sodium sulfinates and N,N-disubstituted formamides
Bao, Xiaodong,Rong, Xiaona,Liu, Zhiguo,Gu, Yugui,Liang, Guang,Xia, Qinqin
supporting information, p. 2853 - 2858 (2018/06/25)
By using formamides as amine sources, a novel and efficient KO-t-Bu mediated amination of sodium sulfinates has been developed. The reaction utilizes readily available starting materials under metal-free conditions, thus providing an alternative and attractive route to sulfonamides.
Simple N,N-dimethyl phenylsulfonamides show potent anticonvulsant effect in two standard epilepsy models
Tanaka, Tomoyuki,Yajima, Nana,Kiyoshi, Tomoko,Miura, Yoshiki,Iwama, Seiji
, p. 94 - 97 (2016/12/09)
Optimization of the previously reported benzothiazine analogue A led to the identification of compound 1, which showed anti-convulsant activity in two golden standard animal models of seizure, the MES and scPTZ models. Structure-activity relationship investigation of compound 1 revealed compounds 2, 6 and 19 as attractive anti-epileptic drug (AED) candidates with potent anticonvulsant effect in both the MES and scPTZ models. As these compounds are structurally different from existing AEDs, determination of their mechanism of actions could provide clues to understanding current therapy-resistant seizures. Moreover, these simple phenylsulfoneamide compounds could be good starting points for searching broad spectrum AEDs by such in vivo screening.
N-Methylation of poorly nucleophilic aromatic amines with dimethyl carbonate
Yan, Huidong,Zeng, Liufang,Xie, Yaqiang,Cui, Yu,Ye, Liyi,Tu, Song
, p. 5951 - 5960 (2016/06/01)
Abstract: Dimethyl carbonate (DMC), an environmentally friendly methylation agent, is a substitute for traditional methylation agents such as methyl halides (CH3X, X?=?I, Br, Cl) or dimethyl sulfate. An efficient, convenient, and green method has been developed for N-methylation of poorly nucleophilic aromatic amines with DMC. It was found that the couple PEG400/K2CO3 provides good selectivity for the N-methylation product. Finally, the mechanism for reaction of amines with DMC was investigated, and a plausible multistep mechanism proposed and verified. Graphical Abstract: [Figure not available: see fulltext.]
Copper-mediated S-N formation via an oxygen-activated radical process: A new synthesis method for sulfonamides
Huang, Xin,Wang, Jichao,Ni, Zhangqin,Wang, Sichang,Pan, Yuanjiang
supporting information, p. 4582 - 4584 (2014/05/06)
Copper-mediated direct S-N formation using readily available starting materials via an oxygen-activated radical process has been developed. This method provides a novel and direct approach for synthesis of sulfonamides under air conditions. the Partner Organisations 2014.
Microwave-assisted efficient methylation of alkyl and arenesulfonamides with trimethylsulfoxonium iodide and KOH
Malik, Sarika,Nadir, Upender K.,Pandey, Pramod S.
, p. 3074 - 3081 (2008/12/22)
A solvent-free synthesis of N-methyl and N,N-dimethylsulfonamides has been achieved by treating the primary and secondary sulfonamides with Me3S+OI- and KOH under microwave irradiation on alumina support. Copyright Taylor & Francis Group, LLC.
PROCESS FOR MAKING SUBSTITUTED ARYL SULFONAMIDES USING AN INDIUM BASED CATALYST SYSTEM
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Page 7, (2008/06/13)
A process for making substituted aryl sulfonamides by sulfamoylation of an activated aromatic compound using an indium compound as a catalyst.
Catalytic arylation of sulfamoyl chlorides: A practical synthesis of sulfonamides
Frost, Christopher G.,Hartley, Joseph P.,Griffin, David
, p. 1928 - 1930 (2007/10/03)
Commercially available indium(III) triflate is shown to be an efficient catalyst for the sulfamoylation of aromatics.
NUCLEAR MAGNETIC RESONANCE AND X-RAY DIFFRACTION STUDIES ON SOME SUBSTITUTED BENZENESULPHONAMIDES
Haekkinen, Anna-Marija,Ruostesuo, Pirko,Kivekaes, Raikko
, p. 815 - 820 (2007/10/02)
Solid-state 13C c.p.-m.a.s. and solution 13C, 15N, and 17O n.m.r. spectra were measured for toluene-p-sulphonamide, N-methyltoluene-p-sulphonamide, NN-dimethyltoluene-p-sulphonamide, p-chlorobenzenesulphonamide, and NN-simethyl-p-chlorobenzenesulphonamide.The 13C c.p.-m.a.s. n.m.r. resonance lines of the carbon atoms bonded to nitrogen show characteristic line broadening with sligthly asymmetric doublet petterns.Some differences are evident in the 13C shielding of the carbon atoms between the solid-state and solution-state spectra.In the solution spectra the 15N and 17O chemical shifts increase in conformity with the polarity order of the amides.The n.m.r. relaxation times of the methyl groups of the compounds were measured as well.The crystal structures of N-methyltoluene-p-sulphonamide and NN-dimethyltoluene-p-sulphonamide were determined by single-crystal X-ray diffraction technique and refined to final R values of 0.056 and 0.044, respectively.Except for some baely significant differences, the bond lengths and angles are similar in the two compounds.The most striking difference is the value of the C-C-S-N torsion angle.