115600-05-0Relevant articles and documents
Stereoselective synthesis of substituted arylsulfonylated 1,3-butadienes and 2-propenoates by sulfonylation of acetylenic ester
Khalili, Gholamhossein
, p. 532 - 538 (2013)
Protonation of the reactive intermediates produced in the reaction between sodium arylsulfinates and two equiv. of dialkyl acetylenedicarboxylates in DMF, by H2O lead to substituted (1E,3E)-1-(arylsulfonyl)-1,3-butadiene-1,2,3,4- tetracarboxylates in moderate yields. A regioselective method for the synthesis of alkyl (E)-3-(arylsulfonyl)-2-propenoates is described. These reactions provide a useful synthetic route to highly functionalized 1,3-butadienes and 2-propenoates.
Regio- and Stereoselective Hydrosulfonylation of Electron-Deficient Alkynes: Access to Both E- and Z-β-Sulfonyl-α,β-Unsaturated Carbonyl Compounds
Zhang, Wei,Johnson, Gabriel M.,Guan, Zhi,He, Yan-Hong
supporting information, p. 4562 - 4570 (2018/10/24)
A metal-free hydrosulfonylation of electron-deficient alkynes with sodium sulfinates or sulfinic acids to access both E- and Z-β-sulfonyl-α,β-unsaturated carbonyl compounds has been developed. We propose that this reaction via a hydroxylallene intermediate delivers the thermodynamically stable E isomer, or via a concerted termolecular AdE3 mechanism affords Z isomer. The stereoselectivity of addition (syn or anti) can be controlled by varying the sulfonyl sources and acidic buffer solutions. This protocol exhibits broad substrate scope for internal or terminal alkynes including various substituted ynones and alkynyl esters. This approach is mild, efficient, operationally simple and easy to be scaled-up. (Figure presented.).
Design and Synthesis of Novel 4-Phenoxyquinolines Bearing 3-Hydrosulfonylacrylamido or 1H-Imidazole-4-carboxamido Scaffolds as c-Met Kinase Inhibitors
Wang, Jiao,Xie, Lijun,Wang, Yu,Wang, Xiaoqiang,Xi, Shuancheng,Zeng, Tianfang,Gong, Ping,Zhai, Xin
, (2017/02/15)
A series of novel 6,7-disubstituted-4-phenoxyquinoline derivatives bearing (E)-3-hydrosulfonylacrylamido or 1H-imidazole-4-carboxamido moieties were designed, synthesized and evaluated for their cytotoxicity against A549, MKN-45, and HT-29 cancer cell lines in vitro. All the target compounds showed moderate to significant cytotoxic activity against the tested cells with IC50 values ranging from 0.13 to 2.65 μM. Five of them were further examined for their inhibitory activity against c-Met kinase, which identified compound 30 as a promising agent (c-Met IC50 = 1.52 nM) with IC50 values of 0.24, 0.45, and 0.13 μM against HT-29, MKN-45, and A549 cells, respectively.
A Mild and Rapid Synthesis of (Z)-β-Sulfonyl Enoates from Sodium Sulfinates and Propargyl Esters
Jiang, Jun,Zou, Huaxu,Yi, Niannian,Wang, Ruijia,Zhang, Hao,Lan, Lixin,Xiang, Jiannan
, p. 1245 - 1250 (2016/12/27)
Water-promoted sulfonylation of propargyl esters leading to highly regioselective and stereoselective formation of (Z)-β-sulfonyl enoates in excellent yields, by a simple, mild, rapid and environmentally benign reaction procedure is reported.
