64326-47-2Relevant academic research and scientific papers
Photoredox Alkenylation of Carboxylic Acids and Peptides: Synthesis of Covalent Enzyme Inhibitors
Kammer, Lisa Marie,Lipp, Benjamin,Opatz, Till
, p. 2379 - 2392 (2019/01/21)
The synthesis of vinyl sulfones and (α,β-unsaturated) nitriles from carboxylic acids was realized through oxidative decarboxylation with 1,4-dicyanoanthracene as an organic photoredox catalyst. Various types of C-radicals are generated and used to construct three different classes of potential covalent protease inhibitors. The procedure is functional group tolerant and applicable to natural products and druglike scaffolds. It may serve for the rapid construction of screening candidates as demonstrated by a three-step synthesis of the known protease inhibitor K11777.
An economical and convenient synthesis of vinyl sulfones
Guan, Zheng-Hui,Zuo, Wei,Zhao, Lian-Biao,Ren, Zhi-Hui,Liang, Yong-Min
, p. 1465 - 1470 (2008/02/05)
A general process for the efficient synthesis of vinyl sulfones has been developed using commercially available sulfinic acid sodium salts and dibromides. A variety of phenyl and methyl vinyl sulfones have been formed in good yields, in the absence of any catalyst. Georg Thieme Verlag Stuttgart.
Facile method for solid-phase synthesis of vinyl sulfones using polystyrene-supported selenomethyl aryl sulfone
Sheng, Shou-Ri,Zhou, Wei,Zhong, Ming-Hua,Liu, Xiao-Ling,Chen, Hui-Zong
, p. 815 - 821 (2007/10/03)
Treatment of novel polystyrene-supported selenomethyl aryl sulfone with LDA followed by alkylation and oxidation elimination efficiently afforded vinyl sulfones in good yields and purities.
The Diels-Alder reactivity of (E)-3-phenylsulfonylprop-2-enenitrile, a cyanoacetylene equivalent
Bradley, Pamela J.,Grayson, David H.
, p. 1794 - 1799 (2007/10/03)
(E)-3-Phenylsulfonylprop-2-enenitrile undergoes facile Diels-Alder reactions, moderate regioselectivity being observed with several unsymmetrical dienes. Danishefsky's diene and furfuryl alcohol react regioselectively. The cycloadducts formed with cyclopentadiene and with anthracene undergo base-catalysed elimination of benzenesulfinic acid to yield α,β-unsaturated nitriles.
Polystyrene-supported selenosulfonates: Efficient reagents for regio- and stereocontrolled synthesis of vinyl sulfones
Qian,Huang
, p. 1913 - 1916 (2007/10/03)
Two novel polystyrene-supported selenosulfonates reagents have been developed. As reagents for boron trifluoride catalyzed or AIBN catalyzed addition to olefins were successfully demonstrated and have been used for regioselective synthesis of vinyl sulfon
NUCLEOPHILIC ADDITIONS TO α,β-UNSATURATED SULPHONES. III. REGIOCHEMISTRY OF THE REACTION OF (E)-β-CYANOVINYL PHENYL SULPHONE WITH NITROGEN, OXYGEN AND CARBON NUCLEOPHILES
Benedetti, Fabio,Fabrissin, Silvio,Pricl, Sabrina,Risaliti, Amerigo
, p. 391 - 394 (2007/10/02)
The reactions of the title compound with secondary amines, alcohols, and enamines have been studied.Addition or addition-elimination at either electrophilic position is observed.Regiochemistry is a function of steric and electronic effects and of electrostatic interactions.
