572923-19-4Relevant academic research and scientific papers
Copper-Catalyzed One-Pot Synthesis of N -Aryl Oxazolidinones from Amino Alcohol Carbamates
Mahy, William,Plucinski, Pawel K.,Frost, Christopher G.
, p. 5020 - 5023 (2015/01/08)
An efficient sequential intramolecular cyclization of amino alcohol carbamates followed by Cu-catalyzed cross-coupling with aryl iodides under mild conditions has been developed. The reaction occurred in good yields and tolerated aryl iodides containing functionalities such as nitriles, ketones, ethers, and halogens. Heteroaryl iodides and substituted amino alcohol carbamates were also well tolerated.
CuI/N,N-dimethylglycine-catalyzed synthesis of N-aryloxazolidinones from aryl bromides
Li, Jiaojiao,Zhang, Yihua,Jiang, Yongwen,Ma, Dawei
supporting information; experimental part, p. 3981 - 3983 (2012/08/27)
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.
Cu-catalyzed N-arylation of oxazolidinones: An efficient synthesis of the κ-opioid receptor agonist CJ-15161
Ghosh, Arun,Sieser, Janice E.,Caron, Stephane,Couturier, Michel,Dupont-Gaudet, Kristina,Girardin, Melina
, p. 1258 - 1261 (2007/10/03)
An efficient method for intermolecular N-arylation of oxazolidinones using catalytic copper in the presence of a bidentate ligand is reported. The conditions allow the use of copper and can be used to prepare enantiopure N-aryl β-amino alcohols. A short,
Palladium-catalyzed synthesis of N-aryloxazolidinones from aryl chlorides
Ghosh, Arun,Sieser, Janice E.,Riou, Maxime,Cai, Weiling,Rivera-Ruiz, Luis
, p. 2207 - 2210 (2007/10/03)
(Matrix presented) An efficient method for intermolecular N-arylation of oxazolidinones using Pd2dba3 and various phosphine ligands in the presence of a weak base is reported. The conditions allow the use of cheaper aryl chlorides containing functionalities such as enolizable ketones, amides, etc., which would be incompatible with other coupling methods. The coupling reaction can be used to prepare enantiopure N-aryl β-amino alcohols. Depending on the stereoelectronic nature of the aryl chloride, careful choice of ligand was necessary for the success of these reactions.
