7714-93-4Relevant academic research and scientific papers
Aerobic Copper(II)-catalyzed synthesis of β-hydroxysulfides and selenides from alkenes with disulfides and diselenides
Taniguchi, Nobukazu
, (2022/03/07)
A copper-catalyzed hydroxysulfenylation of alkenes was achieved using disulfides in the presence of n-Bu4NI and H2O. The procedure smoothly proceeded under air atmosphere, and the corresponding β-hydroxysulfides were obtained with regio- and anti-selectivity in good yields. Furthermore, a reaction using diselenides effectively produced the expected β-hydroxyselenides. These reactions could use both chalcogenide groups on dichalcogenides. Further the procedure also worked for hydrosulfenylation using thiols.
A facile sulfenylchlorination of alkenes with Me2SO/(COCl)2
Lan, Liyuan,Gao, Yang,Ding, Rui,Zhang, Ting,Liu, Yongguo,Sun, Baoguo,Tian, Hongyu
supporting information, p. 539 - 549 (2019/02/01)
The sulfenylchlorination of a series of alkenes is investigated by using the combined reagent of dimethyl sulfoxide and oxalyl chloride. The corresponding β-chloro sulfides were obtained in mediate to good yields. Most of the terminal alkenes give the Mar
Metal-Free Chlorothiolation of Alkenes Using HCl and Sulfoxides
Ebule, Rene,Hammond, Gerald B.,Xu, Bo
supporting information, p. 4705 - 4708 (2018/09/06)
We report a novel method for the chlorothiolation of alkenes using HCl and sulfoxides to achieve the 1,2-difunctionalization of unactivated alkenes. The combination of our new HCl reagent (HCl/DMPU) with sulfoxides forms a unique chlorothiolation system.
Tetrahydroindazoles as interleukin-2 inducible T-cell kinase inhibitors. Part II. Second-generation analogues with enhanced potency, selectivity, and pharmacodynamic modulation in vivo
Burch, Jason D.,Barrett, Kathy,Chen, Yuan,DeVoss, Jason,Eigenbrot, Charles,Goldsmith, Richard,Ismaili, M. Hicham A.,Lau, Kevin,Lin, Zhonghua,Ortwine, Daniel F.,Zarrin, Ali A.,McEwan, Paul A.,Barker, John J.,Ellebrandt, Claire,Kordt, Daniel,Stein, Daniel B.,Wang, Xiaolu,Chen, Yong,Hu, Baihua,Xu, Xiaofeng,Yuen, Po-Wai,Zhang, Yamin,Pei, Zhonghua
, p. 3806 - 3816 (2015/05/27)
The medicinal chemistry community has directed considerable efforts toward the discovery of selective inhibitors of interleukin-2 inducible T-cell kinase (ITK), given its role in T-cell signaling downstream of the T-cell receptor (TCR) and the implications of this target for inflammatory disorders such as asthma. We have previously disclosed a structure- and property-guided lead optimization effort which resulted in the discovery of a new series of tetrahydroindazole-containing selective ITK inhibitors. Herein we disclose further optimization of this series that resulted in further potency improvements, reduced off-target receptor binding liabilities, and reduced cytotoxicity. Specifically, we have identified a correlation between the basicity of solubilizing elements in the ITK inhibitors and off-target antiproliferative effects, which was exploited to reduce cytotoxicity while maintaining kinase selectivity. Optimized analogues were shown to reduce IL-2 and IL-13 production in vivo following oral or intraperitoneal dosing in mice.
NH4I-mediated three-component coupling reaction: Metal-free synthesis of β-alkoxy methyl sulfides from DMSO, alcohols, and styrenes
Gao, Xiaofang,Pan, Xiaojun,Gao, Jian,Jiang, Huanfeng,Yuan, Gaoqing,Li, Yingwei
supporting information, p. 1038 - 1041 (2015/03/30)
A novel synthesis recipe for β-alkoxy methyl sulfides was developed via NH4I-mediated three-component oxysulfenylation reaction of styrenes with DMSO and alcohols. This method features simple operation and readily available starting materials, and it provides an alternative sulfenylating agent generated from DMSO for oxysulfenylation reactions.
Ammonium iodide-induced sulfonylation of alkenes with DMSO and water toward the synthesis of vinyl methyl sulfones
Gao, Xiaofang,Pan, Xiaojun,Gao, Jian,Huang, Huawen,Yuan, Gaoqing,Li, Yingwei
supporting information, p. 210 - 212 (2015/01/09)
A novel ammonium iodide-induced sulfonylation of alkenes with DMSO and water toward the synthesis of vinyl methyl sulfones is described. The process proceeded smoothly under metal-free conditions with high stereoselectivity and good functional group toler
NaOH-promoted thiolysis of oxiranes using 2-[bis(alkylthio)methylene]-3- oxo-N-o-tolylbutanamides as odorless thiol equivalents
Yu, Haifeng,Dong, Dewen,Ouyang, Yan,Wang, Yan,Liu, Qun
, p. 151 - 155 (2008/03/13)
A convenient and efficient protocol for the thiolysis of oxiranes using 2-[bis(alkylthio)methylene]-3-oxo-N-o-tolylbutanamides as thiol equivalents has been developed. Promoted by sodium hydroxide (NaOH) in ethanol at room temperature, the cleavage commences and the generated thiolate anions undergo nucleophilic addition in situ. β-Hydroxy Sulfides were obtained in high yields along with good β-regioselectivity, and trans β-hydroxy Sulfides were also isolated. The thiolysis of one α,β-epoxyketone product with the thiol equivalents was accomplished to afford the corresponding α-carbonyl sulfides in excellent yields. In all the cases, 3-oxo-N-o-tolylbutanamide, the precursor of the thiol equivalents, could be recovered in the novel thiolysis process as a byproduct in good yield. Georg Thieme Verlag Stuttgart.
4-hydroxycoumarin derivatives. Part XIII (1). 3-(2'-alkylthioethyl-1'-phenyl)-4-hydroxycoumarins and their oxidation products
Sulko, Jerzy
, p. 319 - 324 (2007/10/03)
3-(2'-Methylthioethyl-1'-phenyl)-4-hydroxycoumarin and 3-(2'-ethylthioethyl-1'-phenyl)-1-hydroxycoumarin were synthesized. Acetylation of these compounds with acetic anhydride and pyridine yielded respective 4-acetylcoumarins while appropriate sulfoxides and sulfones were obtained by oxidation of alkylthio substituens with H2O2. 3-(2'-ethylthioethyl-1'-phenyl)-4-hydroxycoumarin methylated with diazomethane gave 3-(2'-ethylthioethyl-1'-phenyl)-4-methoxycoumarin and 2-methoxy-3-(2'-ethylthioethyl-1'-phenyl)-chromone.
Direct deprotonation of aliphatic sulfides
Liu, Yunqi,Glass, Richard S.
, p. 8615 - 8618 (2007/10/03)
Alkylmethyl sulfides are regioselectively deprotonated by n-butyllithium and potassium tert-butoxide at the methyl group in good yields. Thiolane and thiane are deprotonated under the same conditions at the α-position in good yield.
Enantioselective Oxidation of β-Hydroxythioethers. Synthesis of Optically Active Alcohols and Epoxides
Conte, V.,Furia, F. Di,Licini, G.,Modena, G.,Sbampato, G.,Valle, G.
, p. 257 - 276 (2007/10/02)
Optically pure β-hydroxysulfoxides may be obtained by direct oxidation of the parent thioethers with the modified Sharpless reagent developed in our laboratory.Necessary requisites for a successful asymmetric oxidation are both the protection of the OH function and the largest possible difference in size of the two groups linked to the thioether sulfur.This latter condition is fulfilled by using S-methyl derivatives.Examples referring to the oxidation of various S-methyl-β-hydroxythioethers, characterized by e.e. values up to 80percent, which may be further increased (>98percent) by crystallization, are presented.Results concerning the synthesis of optically active epoxides and alcohols starting from β-hydroxysulfoxides are also presented which, in some cases, allows the absolute configuration of the parent sulfoxide to be established.
