7108-41-0Relevant articles and documents
Catalyst-Free Singlet Oxygen-Promoted Decarboxylative Amidation of α-Keto Acids with Free Amines
Xu, Wen-Tao,Huang, Bei,Dai, Jian-Jun,Xu, Jun,Xu, Hua-Jian
, p. 3114 - 3117 (2016)
A novel catalyst-free decarboxylative amidation of α-keto acids with amines under mild conditions has been developed. Advantages of the new protocol include avoidance of metal catalysts and high levels of functional group tolerance. In addition, the reaction can be scaled up and shows high chemoselectivity. Preliminary mechanistic studies suggest that singlet oxygen, generated from oxygen under irradiation, is the key promoter for this catalyst-free transformation.
Preparation method of N-aryl amide compound
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Paragraph 0035-0039, (2020/07/13)
The invention discloses a preparation method of an N-aryl amide compound, which comprises the following steps: (1) putting diaryliodonium salt and Cu(OAc)2 into a Schlenk tube provided with a magneticstirring rod; (2) sequentially adding DCE, H2O and nitrile by using an injector, sealing the Schlenk tube, and stirring for reaction at 80 DEG C; (3) cooling the obtained solution to room temperature, and performing extraction with EtOAc; and combining organic layers, performing washing with saline water, and performing drying with anhydrous Na2SO4; and (4) removing volatile matters in vacuum, and purifying residues through column chromatography to obtain the N-aryl amide compound. Through a large number of experiments, a substrate with a simple structure is screened, the reaction conditionsare mild, the yield is high, the pollution is small, and the application prospect is wide.
Cyclization of N-arylcyclopropanecarboxamides into N-arylpyrrolidin-2-ones under electron ionization and in the condensed phase
Lebedev, A. T.,Mazur, D. M.,Kudelin, A. I.,Fedotov, A. N.,Gloriozov, I. P.,Ustynyuk, Yu. A.,Artaev, V. B.
, p. 2416 - 2422 (2016/10/22)
Rationale: Mass spectrometry is known as an excellent method to predict the behavior of organic compounds in solution. The behavior of organic compounds in the gas phase inside the ion source of a mass spectrometer allows their intrinsic properties to be defined, avoiding the influence of intermolecular interactions, counter ions and solvent effects. Methods: Arylpyrrolidin-2-ones were obtained by condensed-phase synthesis from the corresponding N-arylcyclopropanecarboxamides. Electron ionization (EI) with accurate mass measurements by high-resolution time-of-flight mass-spectrometry and quantum chemical calculations were used to understand the behavior of the molecular radical cations of N-arylcyclopropanecarboxamides and N-arylpyrrolidin-2-ones in the ion source of a mass spectrometer. The geometries of the molecules, transition states, and intermediates were fully optimized using DFT-PBE calculations. Results: Fragmentation schemes, ion structures, and possible mechanisms of primary isomerisation were proposed for isomeric N-arylcyclopropanecarboxamides and N-arylpyrrolidin-2-ones. Based on the fragmentation pattern of the N-arylcyclopropanecarboxamides, isomerisation of the original M+? ions into the M+? ions of the N-arylpyrrolidin-2-ones was shown to be only a minor process. In contrast, this cyclization proceeds easily in the condensed phase in the presence of Br?nsted acids. Conclusions: Based on the experimental data and quantum chemical calculations the principal mechanism of decomposition of the molecular ions of N-arylcyclopropanecarboxamides involves their direct fragmentation without any rearrangements. An alternative mechanism is responsible for the isomerisation of a small portion of the higher energy molecular ions into the corresponding N-arylpyrrolidin-2-one ions. Copyright
