94298-74-5Relevant academic research and scientific papers
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.
Autotandem Catalysis: Inexpensive and Green Access to Functionalized Ketones by Intermolecular Iron-Catalyzed Amidoalkynylation/Hydration Cascade Reaction via N-Acyliminium Ion Chemistry
Abdallahi, Sidi Mohamed,Ewies, Ewies F.,El-Shazly, Mohamed,Ould Elemine, Brahim,Hadou, Abderrahmane,Moncol, Ján,Lawson, Ata Martin,Daich, Adam,Othman, Mohamed
supporting information, p. 15440 - 15449 (2021/10/07)
Iron-based catalysts were applied in cascade-type reactions for the synthesis of different carbonyl compounds. The reactions proceeded by a new iron-catalyzed cascade of alkynylation/hydration by using both the σ- and π-Lewis acid properties of iron salts. The alkynylation reactions of several endo and exocyclic acetoxylactams were achieved with three different catalysts including FeCl3 ? 6H2O, FeCl3, and Fe(OTf)3 showing the efficiency of σ-Lewis acidity of iron (III) salts in catalyzing the alkynylation reaction. We also demonstrated that the reaction sequence could be shortened by the direct use of hydroxylactams, leading to an environmentally friendly protocol, avoiding the need to perform unnecessary lengthy steps. A combination of the hard/soft iron Lewis acid properties was then used to implement an unprecedented tandem intermolecular alkynylation/intramolecular hydration sequence allowing expedient access to a new carbonyl structures from trivial materials.
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
supporting information, 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.
Oxidative C-S bond cleavage reaction of DMSO for C-N and C-C bond formation: New Mannich-type reaction for β-amino ketones
Sun, Kai,Lv, Yunhe,Zhu, Zhonghong,Zhang, Liping,Wu, Hankui,Liu, Lin,Jiang, Yongqing,Xiao, Beibei,Wang, Xin
, p. 3094 - 3097 (2015/02/05)
A novel oxidative C-S bond cleavage reaction of DMSO for N-methylation and subsequent C-C bond formation is described. A series of aryl ketones as well as acetone derivatives could be selectively converted into the corresponding β-amino ketones. Mechanistic studies suggested that N-methylation between imine and DMSO was involved in the reaction.
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.
