Transition Metal-Free Synthesis of meta-Bromo- and meta-Trifluoromethylanilines from Cyclopentanones by a Cascade Reaction |
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Authors: | Dr. Markus Staudt Dr. Adnan Cetin Prof. Lennart Bunch |
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Affiliation: | 1. Department of Drug Design and Pharmacology, Faculty of Health and Medical Sciences, University of Copenhagen, 2100 Copenhagen Ø, Denmark;2. Department of Drug Design and Pharmacology, Faculty of Health and Medical Sciences, University of Copenhagen, 2100 Copenhagen Ø, Denmark Department of Sciences, Faculty of Education, University of Muş Alparslan, 49250 Muş, Turkey |
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Abstract: | Anilines are key constituents in biologically active compounds and often obtained from transition metal-catalyzed coupling of an aryl halide with an amine. In this work, we report a transition metal-free method for the synthesis of meta-bromo- and meta-trifluoromethylanilines starting from 3-tribromomethylcyclopentanone or 3-(2-bromo-2-chloro-1,1,1-trifluoroethyl)cyclopentanone, respectively. The scope of the transformation is shown by application of primary, secondary and aromatic amines. The reaction proceeds in acceptable to high yields (20–81 %), and allows for the synthesis of anilines with substitution patterns otherwise difficult to access. |
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Keywords: | anilines drug synthesis electrocyclic ring-opening new methodology transition metal-free |
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