- The Synthesis of 3-Aryl-2-oxazolidinones from CO2, Ethylene Oxide, and Anilines Under Mild Conditions Using PVA-DFNT/Ni
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Abstract: A novel nanocatalyst design using nanomaterials through active-zone crystallisation was proposed. The hydrothermal crystallisation of amorphous dendritic fibrous nano-titanium dioxide with Ni (DFNT/Ni) sites was determined to be the main step in producing extremely active dendritic DFNT/Ni zones, which in turn dramatically enhanced their catalytic activities. DFNT/Ni was then combined with polyvinyl alcohol (PVA) by using a traditional individual-nozzle electrospinning method, and the resulting material was named PVA-DFNT/Ni. This method was utilised to produce 3-aryl-2-oxazolidinones from ethylene oxide, CO2, and anilines. The prepared catalytic apparatus was eco-friendly and had the advantages of high catalytic activity, ability to improve the reaction mixture, and reusability without a considerable decrease in efficiency. It is extracted in the straight and adoptive chemical fixation of flue-gas CO2 obtained from industrial emissions, thereby achieving high degrees of CO2 absorption and conversion. Graphic Abstract: [Figure not available: see fulltext.].
- Lu, Jingjing,Liu, Haitao,Xu, Tiejun,Shamsa, Farzaneh
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p. 281 - 292
(2020/07/08)
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- Method for synthesizing N - aryl oxazolidine -2 - ketone compound by ionic liquid catalysis
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The invention discloses a method for catalytic synthesis of a N-aryloxazolane-2-one compound or a chiral N-aryloxazolane-2-one compound from an ionic liquid. The process of the preparation method is as follows: a catalytic amount of ionic liquid is added
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Paragraph 0031-0032; 0095-0096
(2019/10/01)
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- Synthesis of Oxazolidinones and Derivatives through Three-Component Fixation of Carbon Dioxide
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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
- Mei, Congmin,Zhao, Yibo,Chen, Qianwei,Cao, Changsheng,Pang, Guangsheng,Shi, Yanhui
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p. 3057 - 3068
(2018/06/04)
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- Spirulina (Arthrospira) platensis Supported Ionic Liquid as a Catalyst for the Synthesis of 3-Aryl-2-oxazolidinones from Carbon Dioxide, Epoxide, Anilines
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Abstract: This study investigates the potential application of the (Ammonio)butane-1-sulfonate modified Spirulina (Arthrospira) platensis biomasses in the synthesis of 3-aryl-2-oxazolidinones from CO2, ethylene oxide, and anilines. High catalytic activity and ease of recovery from the reaction mixture using filtration and several reuse times without significant losses in performance are additional eco-friendly attributes of this catalytic system. The effects of the structure of ionic liquid on the catalytic performance were investigated and the various reaction conditions were optimized. This observation was exploited in the direct and selective chemical fixation of CO2, affording high degrees of CO2 capture and conversion. Graphical Abstract: [Figure not available: see fulltext.].
- Sadeghzadeh, Seyed Mohsen,Zhiani, Rahele,Emrani, Shokufe
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p. 119 - 124
(2017/10/30)
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- Synthesis of N-aryl-2-oxazolidinones from cyclic carbonates and aromatic amines catalyzed by bio-catalyst
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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.
- Mei, Congmin,Zhao, Yibo,Zou, Ke,Cao, Changsheng,Pang, Guangsheng,Shi, Yanhui
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p. 2179 - 2194
(2017/12/28)
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- A straightforward one-pot synthesis of bioactive: N -aryl oxazolidin-2-ones via a highly efficient Fe3O4@SiO2-supported acetate-based butylimidazolium ionic liquid nanocatalyst under metal- and solvent-free conditions
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In the present study, we report the fabrication and characterization of novel acetate-based butylimidazolium ionic liquid immobilized silica-coated magnetic nanoparticles (IL-OAc@FSMNP). The synthesized nanocomposite proves its supremacy as an environmentally benign catalyst in the reaction of aniline and its derivatives with ethylene carbonate to form bioactive N-aryl oxazolidin-2-ones under metal-, ligand-, and solvent-free conditions. The catalyst offers excellent assemblies of hydrogen-bond donors and acceptors, which activate the substrates, thereby delivering good-to-excellent product yields with a conversion and selectivity of more than 99%. Additionally, mild reaction conditions, wide substrate scope, effortless catalytic recovery and recyclability of the catalyst up to eight consecutive cycles offer the potential for scale-up in various pharmaceutical applications.
- Gupta, Radhika,Yadav, Manavi,Gaur, Rashmi,Arora, Gunjan,Sharma, Rakesh Kumar
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p. 3801 - 3812
(2017/08/22)
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- 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
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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.
- Niemi, Teemu,Perea-Buceta, Jesus E.,Fernández, Israel,Hiltunen, Otto-Matti,Salo, Vili,Rautiainen, Sari,R?is?nen, Minna T.,Repo, Timo
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supporting information
p. 10355 - 10359
(2016/07/22)
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- DBU and DBU-Derived Ionic Liquid Synergistic Catalysts for the Conversion of Carbon Dioxide/Carbon Disulfide to 3-Aryl-2-oxazolidinones/[1,3]Dithiolan-2-ylidenephenyl- Amine
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An intermolecular synergistic catalytic combination of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and a DBU-derived bromide ionic liquid has been developed for the conversion of CO2, epoxides, and amines under metal- And solvent-free conditions. Various 3-aryl-2-oxazolidinones are produced in moderate to excellent yields within a short reaction time. NMR spectroscopy and DFT calculations demonstrate that DBU as a hydrogen bond acceptor and the ionic liquid as a hydrogen bond donor activate the substrates cooperatively by inducing hydrogen bonds to promote the reaction effectively. Based on these results, a possible reaction mechanism on the synergistic catalysis of DBU and the ionic liquid is proposed. In addition, the reaction of CS2, ethylene oxide, and aniline catalyzed by the combination of DBU and the DBU-derived ionic liquid also proceeds smoothly, which opens a hitherto unreported route to [1,3]dithiolan-2-ylidenephenylamine in a straightforward way.
- Wang, Binshen,Luo, Zhoujie,Elageed, Elnazeer H. M.,Wu, Shi,Zhang, Yongya,Wu, Xiaopei,Xia, Fei,Zhang, Guirong,Gao, Guohua
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p. 830 - 838
(2016/03/05)
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- Selective Synthesis of 5-Substituted N-Aryloxazolidinones by Cycloaddition Reaction of Epoxides with Arylcarbamates Catalyzed by the Ionic Liquid BmimOAc
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A selective procedure for the synthesis of 5-substituted N-aryloxazolidinones by the coupling of epoxides with arylcarbamates catalyzed by ionic liquids has been developed. The effects of reaction time, reactant molar ratio, amount of catalyst, and temper
- Elageed, Elnazeer H. M.,Chen, Bihua,Wang, Binshen,Zhang, Yongya,Wu, Shi,Liu, Xiuli,Gao, Guohua
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supporting information
p. 3650 - 3656
(2016/07/28)
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- BmimOAc ionic liquid: A highly efficient catalyst for synthesis of 3-aryl-2-oxazolidinones by direct condensation of 2-(arylamino) alcohols with diethyl carbonate
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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.
- Elageed, Elnazeer H.M.,Wang, Binshen,Zhang, Yongya,Wu, Shi,Gao, Guohua
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p. 271 - 277
(2015/09/01)
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- Bis-aryl urea derivatives as potent and selective LIM kinase (Limk) inhibitors
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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.
- 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
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p. 1846 - 1861
(2015/04/21)
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- One-pot conversion of carbon dioxide, ethylene oxide, and amines to 3-aryl-2-oxazolidinones catalyzed with binary ionic liquids
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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
- Wang, Binshen,Elageed, Elnazeer H.M.,Zhang, Dawei,Yang, Sijuan,Wu, Shi,Zhang, Guirong,Gao, Guohua
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p. 278 - 283
(2014/01/23)
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- CuI/N,N-dimethylglycine-catalyzed synthesis of N-aryloxazolidinones from aryl bromides
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CuI/N,N-dimethylglycine catalyzed coupling of aryl bromides with substituted oxazolidinones took place at 120 °C in DMF, affording the corresponding N-arylation products with good to excellent yields. A number of functional groups, such as ketone, nitrile, nitro, methoxy, and hydroxyl were tolerated under these conditions, thereby allowing diversity synthesis of N-aryloxazolidinones.
- Li, Jiaojiao,Zhang, Yihua,Jiang, Yongwen,Ma, Dawei
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supporting information; experimental part
p. 3981 - 3983
(2012/08/27)
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- Novel syntheses of N-aryloxazolidin-2-ones via tandem reactions of vinyl sulfonium salts
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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
- Xie, Chunsong,Han, Deyu,Liu, Jinhua,Xie, Tian
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experimental part
p. 3155 - 3158
(2010/03/26)
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- Copper-catalyzed C-N coupling of amides and nitrogen-containing heterocycles in the presence of cesium fluoride
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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
- Phillips, Dean P.,Zhu, Xue-Feng,Lau, Thomas L.,He, Xiaohui,Yang, Kunyong,Liu, Hong
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experimental part
p. 7293 - 7296
(2010/03/03)
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- Short and practical synthesis of N′,N′-disubstituted N-aryl-1,2-ethylene-diamines by a decarboxylative ring-opening reaction under nucleophilic conditions
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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
- Morita, Yasuhiro,Ishigaki, Takeshi,Kawamura, Kuniaki,Iseki, Katsuhiko
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p. 2517 - 2523
(2008/02/13)
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- Copper-catalyzed N-arylation of 2-oxazolidinones. An expeditious route to toloxatone
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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.
- Cacchi, Sandro,Fabrizi, Giancarlo,Goggiamani, Antonella
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p. 505 - 512
(2007/10/03)
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- Pd-catalyzed intermolecular amidation of aryl halides: The discovery that xantphos can be trans-chelating in a palladium complex
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A general method for the intermolecular coupling of aryl halides and amides using a Xantphos/ Pd catalyst is described. This system displays good functional group compatibility, and the desired C-N bond forming process proceeds in good to excellent yields with 1-4 mol % of the Pd catalyst. Additionally, the arylation of sulfonamides, oxazolidinones, and ureas is reported. The efficiency of these transformations was found to be highly dependent on reaction concentrations and catalyst loadings. A Pd complex resulting from oxidative addition of 4-bromobenzonitrile, (Xantphos)Pd(4-cyanophenyl)(Br) (II), was prepared in one step from Xantphos, Pd2(dba)3, and the aryl bromide. Complex II proved to be an active catalyst for the coupling between 4-bromobenzonitrile and benzamide. X-ray crystallographic analysis of II revealed a rare trans-chelating bisphosphine-Pd(II) structure with a large bite angle of 150.7°.
- Yin, Jingjun,Buchwald, Stephen L.
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p. 6043 - 6048
(2007/10/03)
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- Synthesis and Spectral Behavior of 5-Methyl-3-phenyl-1,3-oxazolidin-2-ones Using NMR
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Heterocyclic compounds of four 5-methyl-3-phenyl-1,3-oxazolidin-2-ones have been synthesized by the reaction of N-2-hydroxyethyl- or N-2-hydroxypropylanilines with phosgene in the presence of pyridine.From the spectral behavior, the title compounds are found to exist in the trans and cis forms.
- Nishiyama, Tomihiro,Matsui, Shigeki,Yamada, Fukiko
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p. 1427 - 1429
(2007/10/02)
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