- Catalytic Dealkylative Synthesis of Cyclic Carbamates and Ureas via Hydrogen Atom Transfer and Radical-Polar Crossover
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Guided by the transition-metal hydrogen atom transfer and radical-polar crossover concepts, we developed a functional-group-tolerant and scalable method for the synthesis of cyclic carbamates and ureas, which are found in the structures of bioactive compo
- Nagai, Takuya,Mimata, Nao,Terada, Yoshihiro,Sebe, Chikayoshi,Shigehisa, Hiroki
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supporting information
p. 5522 - 5527
(2020/07/24)
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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; 0097-0098
(2019/10/01)
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- Bifunctional organocatalysts for the conversion of CO2, epoxides and aryl amines to 3-aryl-2-oxazolidinones
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A route to synthesize 3-aryl-2-oxazolidinones is developed, which is achieved through a three component reaction between CO2, aryl amines, and epoxides with a binary organocatalytic system composed of organocatalysts and DBU (1,8-diazabicyclo[5.4.0]undec-7-ene). The method allows wide scopes of epoxide and aryl amine substrates with various functional groups under mild reaction conditions. The control experiments indicate that a cyclic carbonate is formed via cycloaddition of epoxides with CO2, which further reacts with the β-amino alcohol originating from epoxides and aryl amines, resulting in the formation of 3-aryl-2-oxazolidinones finally.
- Xie, Ya-Fei,Guo, Cheng,Shi, Lei,Peng, Bang-Hua,Liu, Ning
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supporting information
p. 3497 - 3506
(2019/04/14)
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- Enzyme- and ruthenium-catalyzed dynamic kinetic resolution involving cascade alkoxycarbonylations for asymmetric synthesis of 5-Substituted N-Aryloxazolidinones
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Asymmetric synthesis of N-aryloxazolidinones via dynamic kinetic resolution was developed. A ruthenium-based catalyst was used in the racemization of β-anilino alcohols, while Candida antarctica lipase B (CAL-B) was applied for two selective alkoxycarbony
- Zhang, Yang,Xie, Sheng,Yan, Mingdi,Ramstr?m, Olof
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p. 138 - 144
(2019/04/10)
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- Metal-Organic Framework MIL-101-NH2-Supported Acetate-Based Butylimidazolium Ionic Liquid as a Highly Efficient Heterogeneous Catalyst for the Synthesis of 3-Aryl-2-oxazolidinones
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A novel heterogeneous catalyst, the ionic liquid (IL) of 1-butyl-3-methylimidazolium acetate (BmimOAc) immobilized on MIL-101-NH2, denoted as IL(OAc-)-MIL-101-NH2, was prepared by the "ship-in-a-bottle" strategy. The IL of
- Chong,Wang,Cheng,Lv,Ji
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p. 495 - 503
(2019/01/14)
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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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- Transformation of Carbon Dioxide into Oxazolidinones and Cyclic Carbonates Catalyzed by Rare-Earth-Metal Phenolates
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Rare-earth-metal complexes stabilized by amine-bridged tri(phenolato) ligands were developed, and their activities in catalyzing transformations of CO2 were studied. A series of terminal epoxides and challenging disubstituted epoxides were converted into the respective cyclic carbonates in the presence of CO2 in yields of 58 to 96 %. In addition, these rare-earth-metal complexes also showed good activities in catalyzing three-component reactions of anilines, epoxides, and CO2, which generated 5-substituted-3-aryl-2-oxazolidines in yields of 48 to 96 %, as a useful strategy to construct oxazolidinones.
- Xu, Bin,Wang, Peng,Lv, Min,Yuan, Dan,Yao, Yingming
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p. 2466 - 2471
(2016/08/24)
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- Lipase-catalyzed kinetic resolution of 3-phenyloxazolidin-2-one derivatives: Cascade O- and N-alkoxycarbonylations
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A lipase-catalyzed, cascade kinetic resolution protocol has been established for the synthesis of 3-phenyloxazolidin-2-one derivatives with up to excellent enantioselectivities (95% ee). Candida antarctica lipase B showed high catalytic activity and stere
- Zhang, Yang,Zhang, Yan,Xie, Sheng,Yan, Mingdi,Ramstr?m, Olof
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- A nitrogen bridged three aryloxyacetic-based rare-earth metal compound and its preparation method and application
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The invention discloses a nitrogen bridged triaryloxy rare-earth compound, and a preparation method and catalytic application thereof. The general formula of the rare-earth compound is LLn(THF)3, and the chemical structural formula is disclosed in the spe
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Paragraph 0134-0136
(2017/03/08)
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- Synthesis of Oxazolidinones from Epoxides and Isocyanates Catalyzed by Rare-Earth-Metal Complexes
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Rare-earth-metal complexes stabilized by an amino-bridged triphenolate ligand showed high efficiency in catalyzing the cycloaddition of isocyanates and epoxides in the presence of NBu4I under mild conditions. This strategy is applicable to both
- Wang, Peng,Qin, Jie,Yuan, Dan,Wang, Yaorong,Yao, Yingming
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p. 1145 - 1151
(2015/04/14)
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- Aza-crown ether complex cation ionic liquids: Preparation and applications in organic reactions
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Aza-crown ether complex cation ionic liquids (aCECILs) were devised, fabricated, and characterized by using NMR spectroscopy, MS, thermogravimetric differential thermal analysis (TG-DTA), elemental analysis and physical properties. These new and room-temperature ILs were utilized as catalysts in various organic reactions, such as the cycloaddition reaction of CO2 to epoxides, esterification of acetic acid and alcohols, the condensation reaction of aniline and propylene carbonate, and Friedel-Crafts alkylation of indole with aldehydes were investigated carefully. In these reactions, the ionic liquid exhibited cooperative catalytic activity between the anion and cation. In addition, the aza-[18-C-6HK][HSO4]2 was the best acidic catalyst in the reactions of esterification and Friedel-Crafts alkylation under mild reaction conditions. Jewel in the crown: Nine new and room-temperature aza-crown ether complex ionic liquids (aCECILs) composed of multiple cations and anions were fabricated through a convenient procedure (see scheme). Some of them were used as catalysts in various organic reactions, such as the cycloaddition reaction of CO2 to propylene oxide, esterification of acetic acid and alcohols, the condensation of aniline and propylene carbonate, and Friedel-Crafts alkylation of indole with aldehydes.
- Song, Yingying,Cheng, Chen,Jing, Huanwang
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p. 12894 - 12900
(2015/03/30)
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- A facile and efficient synthesis of 3-aryloxazolidin-2-ones from isocyanates and epoxides promoted by MgI2 etherate
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We described a mild and efficient procedure for the synthesis of 3-aryloxazolidin-2-ones via the cycloaddition of isocyanates with epoxides in the presence of MgI2 etherate (MgI2(OEt2)n) in good yields. Copyright
- Zhang, Xingxian,Chen, Wei,Zhao, Chengfeng,Li, Cheng,Wu, Xiang,Chen, Wei Z.
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experimental part
p. 3654 - 3659
(2010/12/25)
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- An approach to synthesis of 3-Aryl-2-oxazolidinones and in situ 'click' assembly of 1,2,3-triazole oxazolidinones
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A facile and efficient addition of isocyanates with epoxides in the presence of MgI2 etherate was reported in good yields. The corresponding 2-oxazolidinone could be easily converted into 1,2,3-triazole-oxazolidinone by click reaction in excell
- Zhang, Xingxian,Li, Cheng,Chen, Wei,Wu, Xiang
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experimental part
p. 226 - 228
(2011/07/08)
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- Samarium triiodide catalyzed cycloaddition of epoxides with isocyanates: A facile synthesis of oxazolidinones
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Oxazolidinones were synthesized in high yields via cycloaddition of epoxides with isocyanates catalyzed by samarium triiodide.
- Wu, Hua-Yue,Ding, Jin-Chang,Liu, Yun-Kui
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- Selective α-Cleavage Cycloaddition of Oxiranes with Heterocumulenes Catalyzed by Tetraphenylstibonium Iodide
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A catalytic amount of tetraphenylstibonium iodide (1) promoted unusual cycloadditions of oxiranes with isocyanates or carbodiimides, forming 3,4-disubstituted oxazolidin-2-ones 2 and oxazolidin-2-imines 4 under very mild conditions, respectively.In partic
- Fujiwara, Masahiro,Baba, Akio,Matsuda, Haruo
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p. 1351 - 1357
(2007/10/02)
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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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