- Three-component reaction of small-ring cyclic amines with arynes and acetonitrile
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A novel stereospecific three-component reaction of aziridines and azetidines with arynes and acetonitrile has been developed. The reaction affords N-aryl γ-aminobutyronitriles and δ-aminovaleronitriles that can be used as precursors and congeners of a number of bioactive compounds, such as pregabalin and lergotrile.
- Stephens, David,Zhang, Yu,Cormier, Mathew,Chavez, Gabriel,Arman, Hadi,Larionov, Oleg V.
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supporting information
p. 6558 - 6560
(2013/07/26)
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- Protic onium salts-catalyzed synthesis of 5-aryl-2-oxazolidinones from aziridines and CO2 under mild conditions
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Protic onium salts, e.g. pyridium iodide, proved to be highly efficient and recyclable catalysts for the selective synthesis of 5-aryl-2-oxazolidinones under a CO2 atmosphere at room temperature, presumably due to aziridine activation assisted by hydrogen bonding on the basis of 1H NMR and in situ FT IR under CO2 pressure study.
- Yang, Zhen-Zhen,Li, Yu-Nong,Wei, Yang-Yang,He, Liang-Nian
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supporting information; experimental part
p. 2351 - 2353
(2011/10/31)
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- Polystyrene-supported amino acids as efficient catalyst for chemical fixation of carbon dioxide
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Four new polystyrene-supported amino acids have been synthesized and applied to the chemical fixation of carbon dioxide for the first time. Two series of experiments with polystyrene-supported threonine (PS-Thr) and polystyrene-supported tyrosine (PS-Tyr) as catalyst, respectively, were conducted to study the effect of the reaction conditions on the carboxylation of propylene oxide/carbon dioxide. There was no considerable decrease in the yield of propylene carbonate after the polystyrene-supported amino acids were used five times, indicating that these catalysts are very stable. It was demonstrated that these catalysts were very efficient in the carboxylation of various epoxides and aziridines with carbon dioxide under mild conditions without any solvents. The mechanism for this carboxylation is also discussed.
- Qi, Chaorong,Ye, Jinwu,Zeng, Wei,Jiang, Huanfeng
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supporting information; experimental part
p. 1925 - 1933
(2010/11/04)
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- Quaternary ammonium bromide functionalized polyethylene glycol: A highly efficient and recyclable catalyst for selective synthesis of 5-aryl-2-oxazolidinones from carbon dioxide and aziridines under solvent-free conditions
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(Chemical Equation Presented) A quaternary ammonium bromide covalently bound to polyethylene glycol (PEG, MW = 6000), i.e., PEG6000- (NBu3Br)2, was found to be an efficient and recyclable catalyst for the cycloaddition reaction of aziridines to CO2 under mild conditions without utilization of additional organic solvents or cocatalysts. As a result, 5-aryl-2-oxazolidinone was obtained in high yield with excellent regioselectivity. The catalyst worked well for a wide variety of 1-alkyl-2-arylaziridines. Besides, the catalyst could be recovered by centrifugation and reused without significant loss of catalytic activity and selectivity.
- Du, Ya,Wu, Ying,Liu, An-Hua,He, Liang-Nian
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p. 4709 - 4712
(2008/09/21)
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