94298-74-5Relevant articles and documents
Direct N-methylation reaction using DMSO as one-carbon bridge: Convenient access to heterocycle-containing β-amino ketones
Sun, Kai,Wang, Xin,Jiang, Yongqing,Lv, Yunhe,Zhang, Liping,Xiao, Beibei,Li, Donghui,Zhu, Zhonghong,Liu, Lin
, p. 536 - 539 (2015)
A novel oxidative C-S bond cleavage reaction of DMSO for dual C-C and C-N bond formation is described. A series of acetyl heteroarenes could be selectively converted into the corresponding β-amino ketones, which are frequently found in biologically active compounds and pharmaceuticals. DMSO acted in this reaction not only as the solvent but also as a one-carbon bridge.
1,4-Diazabicyclo[2.2.2]octane-Promoted Aminotrifluoromethylthiolation of α,β-Unsaturated Carbonyl Compounds: N-Trifluoromethylthio-4-nitrophthalimide Acts as Both the Nitrogen and SCF3 Sources
Xiao, Qing,He, Qijie,Li, Juncheng,Wang, Jun
, p. 6090 - 6093 (2016/01/09)
A novel difunctionalization reaction is described. It uses N-trifluoromethylthio-4-nitrophthalimide as the reagent, which serves as both the nitrogen and SCF3 sources. In the presence of DABCO (1,4-diazabicyclo[2.2.2]octane), the nitrogen and SCF3 groups can be incorporated into α,β-unsaturated carbonyl compounds easily and give versatile β-amino ketones and esters in good yields. This difunctionalization reaction features mild reaction conditions, high atom-economy, and efficient access to α-SCF3 amino acids.
Ammonium persulfate activated DMSO as a one-carbon synthon for the synthesis of methylenebisamides and other applications
Mahajan, Pankaj S.,Tanpure, Subhash D.,More, Namita A.,Gajbhiye, Jayant M.,Mhaske, Santosh B.
, p. 101641 - 101646 (2015/12/08)
Activation of DMSO to work as an economical and environmentally benign one-carbon synthon has been achieved by using a bench-top reagent ammonium persulfate for general and efficient access to symmetrical methylenebisamides from primary amides. This methodology was used to achieve a three-component Mannich reaction using acetophenone, saccharin and DMSO to furnish a β-amino ketone. It also provided a metal-free synthesis of thiadiazole and bis(phenyl)methane. Effectively, this method uses DMSO as a safer surrogate to formaldehyde. A mechanism for methylenebisamide formation involving radical intermediates has been proposed based on mechanistic studies.
