- Microwave-Assisted Electrostatically Enhanced Phenol-Catalyzed Synthesis of Oxazolidinones
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An electrostatically enhanced phenol is utilized as a straightforward, sustainable, and potent one-component organocatalyst for the atom-economic transformation of epoxides to oxazolidinones under microwave irradiation. Integrating a positively charged center into phenols over a modular one-step preparation gives rise to a bifunctional system with improved acidity and activity, competent in rapid assembly of epoxides and isocyanates under microwave irradiation in a short reaction time (20-60 min). A careful assessment of the efficacy of various positively charged phenols and anilines and the impact of several factors, such as catalyst loading, temperature, and the kind of nucleophile, on catalytic reactivity were examined. Under neat conditions, this one-component catalytic platform was exploited to prepare more than 40 examples of oxazolidinones from a variety of aryl- and alkyl-substituted epoxides and isocyanates within minutes, where up to 96% yield and high degree of selectivity were attained. DFT calculations to achieve reaction barriers for different catalytic routes were conducted to provide mechanistic understanding and corroborated the experimental findings in which concurrent epoxide ring-opening and isocyanate incorporation were proposed.
- Rostami, Ali,Ebrahimi, Amirhossein,Sakhaee, Nader,Golmohammadi, Farhad,Al-Harrasi, Ahmed
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- Triethylamine Hydroiodide as a Bifunctional Catalyst for the Solvent-Free Synthesis of 2-Oxazolidinones
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Among the wide variety of heterocycles, 2-oxazolidinones are recognized as some of the most important heterocyclic compounds in medicinal chemistry. Therefore, the development of a practical method for their synthesis would be an important development. He
- Nishiyori, Ryuichi,Okuno, Ken,Shirakawa, Seiji
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p. 4937 - 4941
(2020/07/30)
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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; 0063-0064
(2019/10/01)
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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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- Carbon dioxide-based facile synthesis of cyclic carbamates from amino alcohols
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We report herein a straightforward general method for the synthesis of cyclic carbamates from amino alcohols and carbon dioxide in the presence of an external base and a hydroxyl group activating reagent. Utilizing p-toluenesulfonyl chloride (TsCl), the reaction proceeds under mild conditions, and the approach is fully applicable to the preparation of various high value-added 5- and 6-membered rings as well as bicyclic fused ring carbamates. DFT calculations and experimental results indicate a SN2-type reaction mechanism with high regio-, chemo-, and stereoselectivity.
- Niemi, Teemu,Fernández, Israel,Steadman, Bethany,Mannisto, Jere K.,Repo, Timo
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supporting information
p. 3166 - 3169
(2018/03/28)
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- Isocyanurate Formation During Oxazolidinone Synthesis from Epoxides and Isocyanates Catalysed by a Chromium(Salphen) Complex
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Chromium(salphen) complex 10 is found to be a catalyst for the preparation of oxazolidinones from epoxides and isocyanates. Using the optimal reaction conditions (1.5 mol % of chromium(salphen) complex 10 at 80 °C in toluene for 4 hours), six epoxides wer
- Wu, Xiao,Mason, Jess,North, Michael
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p. 12937 - 12943
(2017/09/25)
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- Tetraarylphosphonium Salt-Catalyzed Synthesis of Oxazolidinones from Isocyanates and Epoxides
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Preparation of a range of oxazolidinones, including enantioenriched N-aryl-substituted oxazolidinones, in which tetraarylphosphonium salts (TAPS) catalyze the [3 + 2] coupling reaction of isocyanates and epoxides effectively, is described. The key finding is a Br?nsted acid/halide ion bifunctional catalyst that can accelerate epoxide ring opening with high regioselectivity. Mechanistic studies disclosed that the ylide generated from TAPS, along with the formation of halohydrins, plays a crucial role in the reaction with isocyanates.
- Toda, Yasunori,Gomyou, Shuto,Tanaka, Shoya,Komiyama, Yutaka,Kikuchi, Ayaka,Suga, Hiroyuki
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supporting information
p. 5786 - 5789
(2017/11/10)
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- Direct synthesis of oxazolidin-2-ones from tert-butyl allylcarbamate via halo-induced cyclisation
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A novel synthetic pathway towards the 2-oxazolidinone derivatives involving the halo-induced cyclisation of tert-butyl allyl(phenyl)carbamate was successfully developed. Various halogenating reagents were evaluated under different reaction conditions for the reaction optimisation. Interestingly, the synthetic route to 2-oxazolidinone derivatives containing one halogen atom in the aliphatic site or two halogen atoms including the extra halogen atom substituted in the aryl group at the para position, were thoroughly established for all chloro-, bromo- and iodo compounds. Either halo-unsubstituted-aryl oxazolidinone or p-halo-substituted-aryl oxazolidinone could be selectively produced by selecting the appropriate choices of halogenated reagents and reaction conditions e.g. reaction time and temperature. Toloxatone, a commercial antidepressant, was successfully synthesized by using this developed method.
- Paisuwan, Waroton,Chantra, Thanakrit,Rashatasakhon, Paitoon,Sukwattanasinitt, Mongkol,Ajavakom, Anawat
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p. 3363 - 3367
(2017/05/22)
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- Synthesis of Oxazolidinones from Epoxides and Isocyanates Catalysed by Aluminium Heteroscorpionate Complexes
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The combination of an aluminium(heteroscorpionate) complex and tetrabutylammonium bromide acts as a highly efficient catalyst system for the synthesis of oxazolidinones from epoxides and isocyanates. Twenty two complexes were tested derived from a range o
- Castro-Osma, José A.,Earlam, Amy,Lara-Sánchez, Agustín,Otero, Antonio,North, Michael
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p. 2100 - 2108
(2016/07/07)
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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 0120-0123
(2017/03/08)
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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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- 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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- VanadiumV(salen) catalysed synthesis of oxazolidinones from epoxides and isocyanates
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The combination of a vanadiumV(salen) complex V +O(salen) EtOSO3- and tetrabutylammonium bromide forms a highly active catalyst system for the reaction between epoxides and isocyanates leading to oxazolidinones.
- Beattie, Christopher,North, Michael
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p. 31345 - 31352
(2014/08/05)
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- [(Salcen)CrIII + Lewis base]-catalyzed synthesis of N-aryl-substituted oxazolidinones from epoxides and aryl isocyanates
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[(Salcen)CrIII + Lewis base] was found to be a highly active and selective catalyst system in the [2+3] cycloaddition between epoxides and isocyanates to form 5-oxazolidinones. The reaction proceeds to high yield under mild reaction conditions
- Paddock, Robert L.,Adhikari, Debashis,Lord, Richard L.,Baik, Mu-Hyun,Nguyen, Sonbinh T.
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supporting information
p. 15187 - 15190
(2014/12/11)
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- Bimetallic aluminum(salen) catalyzed synthesis of oxazolidinones from epoxides and isocyanates
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The bimetallic aluminum(salen) complex [Al(salen)]2O is shown to catalyze the synthesis of oxazolidinones from epoxides and isocyanates. The reaction is demonstrated to proceed with overall retention of epoxide stereochemistry, and both aromati
- Baronsky, Thilo,Beattie, Christopher,Harrington, Ross W.,Irfan, Reyhan,North, Michael,Osende, Javier G.,Young, Carl
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p. 790 - 797
(2013/06/27)
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- Chemoselective CaO-mediated acylation of alcohols and amines in 2-methyltetrahydrofuran
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Calcium oxide is proposed as an innocuous acid scavenger for the chemoselective synthesis of amide- and ester-type compounds. Although these molecules have wide spread applications in organic and pharmaceutical chemistry, and a large number of routes have been designed for their synthesis, the development of more efficient and environmentally friendly acylation strategies remains an ongoing challenge. The use of CaO allows for the stoichiometric acylation of primary alcohols in the presence of phenols or tertiary alcohols; amines can also be subjected to acylation reactions in the presence of hydroxyl groups. Chirality is obtained through acylation if the starting material is an optically pure alcohol or if a chiral acylating agent is used. Furthermore, the use of 2-methyltetrahydrofuran (2-MeTHF), a more ecofriendly solvent, leads to maximized yields. This protocol is successfully applied to the synthesis of an interesting N-aryloxazolidin-2-one intermediate for the preparation of linezolid-type compounds.
- Pace, Vittorio,Hoyos, Pilar,Alcántara, Andrés R.,Holzer, Wolfgang
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p. 905 - 910
(2013/07/27)
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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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- Ytterbium (III) triflate catalysed [3 + 2] cycloaddition involving isothiocyanates and epichlorohydrin
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Highly regioselective cycloadditions occur in reactions of substituted isothiocyanates and epichlorohydrin to give N-(5-(chloromethyl)-1,3-oxathiolan- 2-ylidene)anilines catalysed by Yb(OTf)3. The configuration is retained at the chiral centres
- Xie, Yuanyuan,Chen, Xiaodong,Su, Weike
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experimental part
p. 129 - 132
(2009/10/15)
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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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- Stereocontrolled Oxazolidinone Formation by the Addition of 4,5-Disubstituted Iminodioxolane to Oxirane via a Spiro Compound
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4,5-Disubstituted 2-imino-1,3-dioxolanes readily add to oxiranes in the presence of AlCl3, furnishing 1,3-oxazolidin-2-ones in a stereospecific manner, where the configurations of oxiranes and iminodioxolanes are responsible for the configuration of products and the feasibility of the addition, respectively.A preliminary adduct, a spiro compound intermediate, is isolated, and its decomposition to oxazolidinone is demonstrated.
- Baba, Akio,Seki, Kenji,Matsuda, Haruo
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p. 2684 - 2688
(2007/10/02)
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- Regiospecific Introduction of Amino-alkene Functionality into 1,2,3-Triols, 1,3-Dihalogenopropan-2-ols, and 2,3-Dihalogenopropanols promoted by Fluoride Anion
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Regiospecific transformations of 1,2,3-triol, 1,3-dihalogenopropan-2-ol, and 2,3-dihalogenopropanol derivatives into oxazolidin-2-ones and/or oxazol-2(3H)-ones promoted by fluoride anion are described.
- Shimizu, Makoto,Yoshioka, Hirosuke
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p. 689 - 690
(2007/10/02)
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- Cycloaddition Reaction of Heterocumulenes with Oxiranes Catalyzed by an Organotin Iodide-Lewis Base Complex
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Organotin halide-Lewis base complexes are versatile catalysts for the cycloaddition of heterocumulenes with oxiranes and afford good yields of five-membered heterocyclic compounds under mild and neutral conditions.The catalysts are sufficiently active tha
- Shibata, Ikuya,Baba, Akio,Iwasaki, Hiroyuki,Matsuda, Haruo
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p. 2177 - 2184
(2007/10/02)
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- The Cycloaddition of Isocyanates and Carbodiimides to Oxiranes Catalyzed by Organotin Iodide-Lewis Base Complexes
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Various types of five-membered heterocyclic compounds such as 2-iminodioxolanes, 2-oxazolidinones, and 2-iminooxazolidines, can be obtained from the cycloaddition of oxiranes with isocyanates or carbodiimides catalyzed by organotin iodide-Lewis base compl
- Baba, Akio,Shibata, Ikuya,Masuda, Kazuhiro,Matsuda, Haruo
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p. 1144 - 1146
(2007/10/02)
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