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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 |
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| 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 |