5198-47-0Relevant academic research and scientific papers
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
A One-Pot Synthesis of N-Aryl-2-Oxazolidinones and Cyclic Urethanes by the Lewis Base Catalyzed Fixation of Carbon Dioxide into Anilines and Bromoalkanes
Niemi, Teemu,Perea-Buceta, Jesus E.,Fernández, Israel,Hiltunen, Otto-Matti,Salo, Vili,Rautiainen, Sari,R?is?nen, Minna T.,Repo, Timo
supporting information, p. 10355 - 10359 (2016/07/22)
The multicomponent assembly of pharmaceutically relevant N-aryl-oxazolidinones through the direct insertion of carbon dioxide into readily available anilines and dibromoalkanes is described. The addition of catalytic amounts of an organosuperbase such as Barton's base enables this transformation to proceed with high yields and exquisite substrate functional-group tolerance under ambient CO2pressure and mild temperature. This report also provides the first proof-of-principle for the single-operation synthesis of elusive seven-membered ring cyclic urethanes.
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.
Copper-Catalyzed One-Pot Synthesis of N -Aryl Oxazolidinones from Amino Alcohol Carbamates
Mahy, William,Plucinski, Pawel K.,Frost, Christopher G.
supporting information, p. 5020 - 5023 (2015/01/08)
An efficient sequential intramolecular cyclization of amino alcohol carbamates followed by Cu-catalyzed cross-coupling with aryl iodides under mild conditions has been developed. The reaction occurred in good yields and tolerated aryl iodides containing functionalities such as nitriles, ketones, ethers, and halogens. Heteroaryl iodides and substituted amino alcohol carbamates were also well tolerated.
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 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.
3-Aryl-2-oxazolidinones through the palladium-catalyzed N-arylation of 2-oxazolidinones.
Cacchi,Fabrizi,Goggiamani,Zappia
, p. 2539 - 2541 (2007/10/03)
[reaction: see text] 3-Aryl-2-oxazolidinones are obtained in good yields through the palladium-catalyzed N-arylation of 2-oxazolidinones with aryl bromides. The nature of aryl bromides, phosphine ligands, bases, and solvents strongly affects the reaction
