2033-32-1Relevant 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.
BmimOAc ionic liquid: A highly efficient catalyst for synthesis of 3-aryl-2-oxazolidinones by direct condensation of 2-(arylamino) alcohols with diethyl carbonate
Elageed, Elnazeer H.M.,Wang, Binshen,Zhang, Yongya,Wu, Shi,Gao, Guohua
, p. 271 - 277 (2015/09/01)
An efficient convenient procedure for the synthesis of 3-aryl-2-oxazolidinones from 2-(arylamino) alcohols and diethyl carbonate (DEC) catalyzed by ionic liquids is described. The effects of reaction time, amount of catalyst and temperature were investigated. Excellent yields of products were obtained under the optimized reaction conditions, when using BmimOAc as a catalyst. An intermediate ethyl 2-(phenyl amino) ethyl carbonate was isolated and characterized. 1H NMR spectroscopy and DFT calculations indicated that BmimOAc cooperatively activate the substrates through hydrogen bonding with its anion and cation sites. According to these results, a possible reaction mechanism was discussed.
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.
One-pot conversion of carbon dioxide, ethylene oxide, and amines to 3-aryl-2-oxazolidinones catalyzed with binary ionic liquids
Wang, Binshen,Elageed, Elnazeer H.M.,Zhang, Dawei,Yang, Sijuan,Wu, Shi,Zhang, Guirong,Gao, Guohua
, p. 278 - 283 (2014/01/23)
An effective one-pot method for the conversion of carbon dioxide, ethylene oxide, and amines to 3-aryl-2-oxazolidinones has been developed. This one-pot method consists of two parallel reactions and a subsequent cascade reaction between the two products of the corresponding parallel reactions. Notably, the binary ionic liquids of 1-butyl-3-methyl-imidazolium bromide and 1-butyl-3-methyl-imidazolium acetate demonstrate a synergistic catalytic effect on this new strategy. 1-Butyl-3-methyl-imidazolium bromide is essential in two parallel reactions owing to the good nucleophilicity and leaving ability of bromide, and 1-butyl-3-methyl-imidazolium acetate plays a dominant role in the subsequent cascade reaction owing to the strong basicity of acetate. In addition, the binary ionic liquids can be used thrice without significant loss of catalytic activity. Copyright
