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A One‐Pot Synthesis of N‐Aryl‐2‐Oxazolidinones and Cyclic Urethanes by the Lewis Base Catalyzed Fixation of Carbon Dioxide into Anilines and Bromoalkanes
Authors:Teemu Niemi  Dr. Jesus E. Perea‐Buceta  Dr. Israel Fernández  Otto‐Matti Hiltunen  Vili Salo  Sari Rautiainen  Dr. Minna T. Räisänen  Prof. Timo Repo
Affiliation:1. Department of Chemistry, P.O. Box 55, 00014, University of Helsinki, Finland;2. Departamento de Química Orgánica I, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, Ciudad Universitaria, Madrid, Spain
Abstract:The multicomponent assembly of pharmaceutically relevant N‐aryl‐oxazolidinones through the direct insertion of carbon dioxide into readily available anilines and dibromoalkanes is described. The addition of catalytic amounts of an organosuperbase such as Barton's base enables this transformation to proceed with high yields and exquisite substrate functional‐group tolerance under ambient CO2 pressure and mild temperature. This report also provides the first proof‐of‐principle for the single‐operation synthesis of elusive seven‐membered ring cyclic urethanes.
Keywords:2-oxazolidinones  antibiotics  carbon dioxide  density functional calculations  guanidine superbases
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