37072-63-2Relevant academic research and scientific papers
Novel syntheses of N-aryloxazolidin-2-ones via tandem reactions of vinyl sulfonium salts
Xie, Chunsong,Han, Deyu,Liu, Jinhua,Xie, Tian
, p. 3155 - 3158 (2009)
An unprecedented and efficient domino reaction of diphenyl vinyl sulfonium salt with carbamates leading to the syntheses of N-aryloxazolidin-2-ones has been developed. The scope of this transformation has been studied and a plausible mechanism has been pr
Synthesis of N-aryl-2-oxazolidinones from cyclic carbonates and aromatic amines catalyzed by bio-catalyst
Mei, Congmin,Zhao, Yibo,Zou, Ke,Cao, Changsheng,Pang, Guangsheng,Shi, Yanhui
, p. 2179 - 2194 (2017/12/28)
A convenient and effective method of synthesizing 3-aryl-2-oxazolidinones from cyclic carbonates and aryl amines catalyzed by bio-catalyst adenine in the presence of Et3N under solvent-free conditions is described. The protocol is suitable for the wide scope of substrates, e.g. cyclic carbonates with or without substitutes, and aryl amines with either electron-withdrawing or electron-donating group. The products were obtained in good to excellent yields under the optimal conditions, even in steric hindered cases. The effect of reaction time, temperature, loading of catalyst, and amount of starting materials in the reaction were investigated, and the reaction mechanism is discussed.
Synthesis of Oxazolidinones and Derivatives through Three-Component Fixation of Carbon Dioxide
Mei, Congmin,Zhao, Yibo,Chen, Qianwei,Cao, Changsheng,Pang, Guangsheng,Shi, Yanhui
, p. 3057 - 3068 (2018/06/04)
An effective three-component fixation of atmospheric CO2 with readily available 1,2-dichloroethane and aromatic amine toward oxazolidinones catalyzed by in situ NHC was developed. The reaction occurred in good to excellent yields with good gene
Bis-aryl urea derivatives as potent and selective LIM kinase (Limk) inhibitors
Yin, Yan,Zheng, Ke,Eid, Nibal,Howard, Shannon,Jeong, Ji-Hak,Yi, Fei,Guo, Jia,Park, Chul Min,Bibian, Mathieu,Wu, Weilin,Hernandez, Pamela,Park, Hajeung,Wu, Yuntao,Luo, Jun-Li,Lograsso, Philip V.,Feng, Yangbo
, p. 1846 - 1861 (2015/04/21)
The discovery/optimization of bis-aryl ureas as Limk inhibitors to obtain high potency and selectivity and appropriate pharmacokinetic properties through systematic SAR studies is reported. Docking studies supported the observed SAR. Optimized Limk inhibitors had high biochemical potency (IC50 400-fold), potent inhibition of cofilin phosphorylation in A7r5, PC-3, and CEM-SS T cells (IC50 1 μM), and good in vitro and in vivo pharmacokinetic properties. In the profiling against a panel of 61 kinases, compound 18b at 1 μM inhibited only Limk1 and STK16 with ≥80% inhibition. Compounds 18b and 18f were highly efficient in inhibiting cell-invasion/migration in PC-3 cells. In addition, compound 18w was demonstrated to be effective on reducing intraocular pressure (IOP) on rat eyes. Taken together, these data demonstrated that we had developed a novel class of bis-aryl urea derived potent and selective Limk inhibitors.
Dual Bronsted acid/nucleophilic activation of carbonylimidazole derivatives
Heller, Stephen T.,Fu, Tingting,Sarpong, Richmond
supporting information; experimental part, p. 1970 - 1973 (2012/06/01)
Carbonylimidazole derivatives have been found to be highly active acylation reagents for esterification and amidation in the presence of pyridinium salts. These reactions are thought to involve both Bronsted acid and nucleophilic catalysis. This mode of activation has been applied to the synthesis of difficult to access oxazolidinones, as well as esters and amides. Finally, the use of pyridinium salts has been shown to accelerate the esterification of carboxylic acids with imidazole carbamates.
Synthesis, crystal structure and fungicidal activities of new type oxazolidinone-based strobilurin analogues
Li, Yuhao,Liu, Rui,Yan, Zhangwei,Zhang, Xiangning,Zhu, Hongjun
experimental part, p. 3341 - 3347 (2012/05/05)
A series of oxazolidinone-based strobilurin analogues were efficiently synthesized by the reaction of 3-(2-bromomethylphenyl) oxazolidin-2-one with 1-substituted phenyl-2H-pyrazolin-3-one. Their structures were confirmed and characterized by 1H-NMR, 13C-NMR, elemental analysis, and mass spectroscopy. In addition, the crystal structure of the target compound 3-(2-((1-phenyl-2H-pyrazol-3-yloxy)methyl)phenyl) oxazolidin-2-one was determined by single crystal X-ray diffraction. The bioassay results of these compounds indicated that some of the oxazolidin-2-one derivatives containing N-substituted phenyl 2H-pyrazol ring exhibited potential in vivo fungicidal activities against M. grisea at the dosage of 1 g L-1.
An eco-friendly, convenient, and practical conversion of arylamines to oxazolidinones
Gong, Hang,Yang, Nian-Fa,Deng, Guo-Jun,Xu, Guang-Yi
supporting information; experimental part, p. 584 - 585 (2011/04/21)
A one-step procedure for efficient synthesis of oxazolidinone only using ethylene carbonate and arylamines in the presence of 1,4-diazabicyclo[2,2,2] octane (DABCO) was developed. In most cases, moderate to high yield of products were obtained. This reaction can be considered a carbon dioxide fixation reaction since ethylene carbonate was synthesized via reaction of ethylene oxide with carbon dioxide. Copyright
Copper-catalyzed C-N coupling of amides and nitrogen-containing heterocycles in the presence of cesium fluoride
Phillips, Dean P.,Zhu, Xue-Feng,Lau, Thomas L.,He, Xiaohui,Yang, Kunyong,Liu, Hong
supporting information; experimental part, p. 7293 - 7296 (2010/03/03)
The copper-catalyzed C-N coupling of amides to aryl halides usually requires the use of strong alkali metal bases, such as K2CO3, K3PO4, and Cs2CO3, at high temperature. We discovered that
Short and practical synthesis of N′,N′-disubstituted N-aryl-1,2-ethylene-diamines by a decarboxylative ring-opening reaction under nucleophilic conditions
Morita, Yasuhiro,Ishigaki, Takeshi,Kawamura, Kuniaki,Iseki, Katsuhiko
, p. 2517 - 2523 (2008/02/13)
A straightforward and practical synthesis of N′,N′- disubstituted N-aryl-1,2-ethylenediamines, starting from anilines, via N-aryloxazolidin-2-ones is described. A decarboxylative ring-opening reaction of N-aryloxazolidin-2-ones, using aliphatic secondary
Copper-catalyzed N-arylation of 2-oxazolidinones. An expeditious route to toloxatone
Cacchi, Sandro,Fabrizi, Giancarlo,Goggiamani, Antonella
, p. 505 - 512 (2007/10/03)
3-Aryl-2-oxazolidinones are obtained in excellent yields through the copper-catalyzed N-arylation of 2-oxazolidinones with a variety of aryl iodides. With aryl halides containing both iodo and bromo substituents, a high C-I/C-Br selectivity can be achieved. The procedure has been successfully applied to the preparation of a key intermediate in the synthesis of linezolid and to develop an expeditious route to toloxatone.
