99184-18-6Relevant academic research and scientific papers
A Phosphonium Ylide as a Ligand for [3 + 2] Coupling Reactions of Epoxides with Heterocumulenes under Mild Conditions
Hashimoto, Kousuke,Mori, Yoko,Suga, Hiroyuki,Toda, Yasunori
, p. 10980 - 10987 (2020/09/23)
The potential of carbonyl-stabilized phosphonium ylides as ligands for novel catalysis was explored. We found that the combination of phosphonium ylides and metal halide salts efficiently catalyzed the reaction of epoxides with carbon dioxide under mild c
Tetraarylphosphonium Salt-Catalyzed Synthesis of Oxazolidinones from Isocyanates and Epoxides
Toda, Yasunori,Gomyou, Shuto,Tanaka, Shoya,Komiyama, Yutaka,Kikuchi, Ayaka,Suga, Hiroyuki
supporting information, p. 5786 - 5789 (2017/11/10)
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.
Isocyanurate Formation During Oxazolidinone Synthesis from Epoxides and Isocyanates Catalysed by a Chromium(Salphen) Complex
Wu, Xiao,Mason, Jess,North, Michael
, p. 12937 - 12943 (2017/09/25)
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
Direct synthesis of oxazolidin-2-ones from tert-butyl allylcarbamate via halo-induced cyclisation
Paisuwan, Waroton,Chantra, Thanakrit,Rashatasakhon, Paitoon,Sukwattanasinitt, Mongkol,Ajavakom, Anawat
, p. 3363 - 3367 (2017/05/22)
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.
Synthesis of Oxazolidinones from Epoxides and Isocyanates Catalysed by Aluminium Heteroscorpionate Complexes
Castro-Osma, José A.,Earlam, Amy,Lara-Sánchez, Agustín,Otero, Antonio,North, Michael
, p. 2100 - 2108 (2016/07/07)
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
VanadiumV(salen) catalysed synthesis of oxazolidinones from epoxides and isocyanates
Beattie, Christopher,North, Michael
, p. 31345 - 31352 (2014/08/05)
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.
Bimetallic aluminum(salen) catalyzed synthesis of oxazolidinones from epoxides and isocyanates
Baronsky, Thilo,Beattie, Christopher,Harrington, Ross W.,Irfan, Reyhan,North, Michael,Osende, Javier G.,Young, Carl
, p. 790 - 797 (2013/06/27)
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
A facile and efficient synthesis of 3-aryloxazolidin-2-ones from isocyanates and epoxides promoted by MgI2 etherate
Zhang, Xingxian,Chen, Wei,Zhao, Chengfeng,Li, Cheng,Wu, Xiang,Chen, Wei Z.
experimental part, p. 3654 - 3659 (2010/12/25)
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
An approach to synthesis of 3-Aryl-2-oxazolidinones and in situ 'click' assembly of 1,2,3-triazole oxazolidinones
Zhang, Xingxian,Li, Cheng,Chen, Wei,Wu, Xiang
experimental part, p. 226 - 228 (2011/07/08)
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
Samarium triiodide catalyzed cycloaddition of epoxides with isocyanates: A facile synthesis of oxazolidinones
Wu, Hua-Yue,Ding, Jin-Chang,Liu, Yun-Kui
, p. 36 - 37 (2007/10/03)
Oxazolidinones were synthesized in high yields via cycloaddition of epoxides with isocyanates catalyzed by samarium triiodide.
