7355-56-8Relevant academic research and scientific papers
Regioselective C-H Thioarylation of Electron-Rich Arenes by Iron(III) Triflimide Catalysis
Dodds, Amy C.,Sutherland, Andrew
, p. 5922 - 5932 (2021/05/04)
A mild and regioselective method for the preparation of unsymmetrical biaryl sulfides using iron(III) catalysis is described. Activation of N-(arylthio)succinimides using the powerful Lewis acid iron(III) triflimide allowed the efficient thiolation of a range of arenes, including anisoles, phenols, acetanilides, and N-heterocycles. The method was applicable for the late-stage thiolation of tyrosine and tryptophan derivatives and was used as the key step for the synthesis of pharmaceutically relevant biaryl sulfur-containing compounds such as the antibiotic dapsone and the antidepressant vortioxetine. Kinetic studies revealed that while N-(arylthio)succinimides bearing electron-deficient arenes underwent thioarylation catalyzed entirely by iron(III) triflimide, N-(arylthio)succinimides with electron-rich arenes displayed an autocatalytic mechanism promoted by the Lewis basic product.
Sulfoximine- and sulfilimine-based DAPSON analogues; Syntheses and bioactivities
Chen, Xiao Yun,Buschmann, Helmut,Bolm, Carsten
, p. 2808 - 2810 (2013/02/22)
Sulfoximine- and sulfilimine-based diamino-diphenyl sulfone (DAPSON) analogues have been prepared and their COX-1 and COX-2 inhibition potencies as well as LTBand TNF binding properties were studied. Furthermore, their antiproliferative activities on cancer cell growth were investigated. Neither compounds showed significant bioactivities. Copyright
Synthesis and fungicidal activity of bis(2-arylcarbonylamino-1H- benzimidazol-5-yl) sulfones
Pilyugin,Kuznetsova,Sapozhnikov,Chikisheva,Kiseleva,Vorob'eva,Klimakova,Sapozhnikova,Davletov,Galeeva
, p. 446 - 450 (2008/09/19)
A procedure has been developed for the synthesis of bis(2- arylcarbonylamino-1H-benzimidazol-5-yl) sulfones by reaction of the corresponding substituted benzoyl chloride with sodium cyanamide and subsequent treatment of the N-cyanobenzamide thus formed with 3,3′,4,4′- tetraaminodiphenyl sulfone in acid medium. The products were tested for fungicidal activity.
NMR Study of Substituent Effects in 4-Substituted and 4,4'-Disubstituted Diphenyl Sulphides
Chandrasekaran, R.,Perumal, S.,Wilson, D.A.
, p. 1001 - 1006 (2007/10/02)
The proton and carbon NMR spectra of nine 4-X-diphenyl sulphides (series 1), seven 4-X-4'-NO2-diphenyl sulphides (series 2) and eight 4,4'-X2-diphenyl sulphides (series 3) have been obtained.Correlation of the 13C chemical shifts with the appropriate substituent chemical shifts (SCS) for monosubstituted benzenes (Lynch plots) show an enhancement of substituent effect at C-1 (carbon para to the substituent) in series 1 ans 2, but not in series 3.The carbons of the unsubstituted ring in series 1 also correlate with Cp-SCS, with slopes of less than unity; correlation for C-1' has a negative slope.Dual substituent parameter (DSP) correlations of the 13C chemical shifts with ?I/?oR are good to exellent for all the carbons of series 1 compounds, except those ortho to the substituent X.The carbons meta to the substituent X correlate well, but with negative values for ρI and ρR, although showing a scattered Lynch plot.Similar correlations are found with some carbon shifts in series 2, and with C-1 shifts in series 3.It is concluded that (a) reverse resonance effects are operative at the position meta to the variable substituent by virtue of the sulphur substituent ortho to that carbon; (b) there is transmission of inductive (field) and resonance effects from one aryl ring to the other, except when both rings carry substituents of the same electronic character (series 3); (c) there is some evidence for ?-polarization in the unsubstituted phenyl ring of series 1 compounds.Key words 1H NMR 13C NMR Diphenyl sulphides substituent effects
Use of Potassium Bromate. Oxidation of Organic Sulphur Compounds
Adak, Mohini Mohan,Banerjee, Gopal Chandra,Banerjee, Amalendu
, p. 224 - 228 (2007/10/02)
Oxidation of various organic sulphur compounds by potassium bromate under different experimental conditions was studied.
