Synthesis of Oxindoles through Silver-Catalyzed Trifluoromethylation-, Difluoromethylation- and Arylsulfonylation-Cyclization Reaction of<i>N</i>-Arylacrylamides
作者:Jidan Liu、Shaobo Zhuang、Qingwen Gui、Xiang Chen、Zhiyong Yang、Ze Tan
DOI:10.1002/ejoc.201400087
日期:2014.5
Efficient synthesis of trifluoromethyl and difluoromethyl-substituted oxindoles was achieved by reacting Langlois reagent or Baran reagent with N-arylacrylamides. However, the reaction of aryl sulfinic acid sodium salts with N-arylacrylamides did not give the desulfinative products, instead, aryl sulfonated products were produced.
通过 Langlois 试剂或 Baran 试剂与 N-芳基丙烯酰胺反应,实现了三氟甲基和二氟甲基取代的羟吲哚的有效合成。然而,芳基亚磺酸钠盐与N-芳基丙烯酰胺的反应没有得到脱亚磺化产物,而是产生了芳基磺化产物。
Visible-Light-Induced 3-Component Synthesis of Sulfonylated Oxindoles by Fixation of Sulfur Dioxide
(Acr+−Mes ⋅ ClO4−) as catalyst was developed for the synthesis of sulfone‐containing heterocycles including thioflavones, oxindoles, and quinoline‐2,4(1H ,3H )‐diones through the cascade sulfonation/cyclization reactions under the irradiation of blue light at room temperature.
The first facile one‐pot synthesis of sulfone‐containing oxindoles with easily accessible disulfides as the sulfonylating precursors is described. This reaction occurs smoothly under transition metal‐free conditions and shows excellent functional group tolerance, allowing the facile and efficient green synthesis of various sulfone‐containing oxindoles in aqueous solution. Preliminary mechanistic studies
描述了第一个简便的单锅合成含砜的吲哚类化合物,其中二硫醚作为磺酰化的前体很容易获得。该反应在不含过渡金属的条件下可平稳进行,并具有出色的官能团耐受性,可在水溶液中轻松高效地绿色合成各种含砜的羟吲哚。初步的机理研究表明,水(H 2 O)和过硫酸钾(K 2 S 2 O 8)均可以是产物中砜基的氧源。
Catalyst-free direct arylsulfonylation of N-arylacrylamides with sulfinic acids: a convenient and efficient route to sulfonated oxindoles
作者:Wei Wei、Jiangwei Wen、Daoshan Yang、Juan Du、Jinmao You、Hua Wang
DOI:10.1039/c4gc00231h
日期:——
A catalyst-free procedure has been developed for the construction of sulfonated oxindoles via direct arylsulfonylation of activated alkenes with sulfinic acids.