Derivatization of 1-phenyl substituted 4-amino-2-benzazepin-3-ones: evaluation of Pd-catalyzed coupling reactions |
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Authors: | Steven Ballet Bert UW Maes |
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Institution: | a Department of Organic Chemistry, Vrije Universiteit Brussel, Pleinlaan 2, B-1050 Brussels, Belgium b Organic Synthesis, University of Antwerp, Groenenborgerlaan 171, B-2020 Antwerp, Belgium |
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Abstract: | Several Pd-catalyzed reactions were explored to further functionalize the bromo-substituted 4-amino-1,2,4,5-tetrahydro-2-benzazepin-3-one scaffold (Aba). We report in this paper suitable reaction conditions for Suzuki, Buchwald-Hartwig, and Heck reactions. The substitution pattern of the starting aminobenzazepinone turned out to be crucial for the success of these transition metal-catalyzed reactions, which often required modifications of standard literature procedures. The Pd-catalyzed methods provide access to novel substitution patterns of the Aba scaffold. |
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Keywords: | 4-Amino-1 2 4 5-tetrahydro-2-benzazepin-3-ones Pd[0] catalysis Suzuki reaction Buchwald-Hartwig reaction Heck reaction N-Arylation |
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