Desulfonylative radical ring closure onto aromatics. A modular route to benzazepin-2-ones and 5-arylpiperidin-2-ones |
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Authors: | Charrier Nicolas Liu Zhibo Zard Samir Z |
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Institution: | Laboratoire de Synthèse Organique, CNRS UMR 7652 Ecole Polytechnique, 91128 Palaiseau Cedex, France. |
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Abstract: | Adducts from the intermolecular radical addition of N-xanthylacetyl-N-methanesulfanilides to Boc-protected allylamine undergo ring closure with loss of a methanesulfonyl radical to give benzazepin-2-ones. Upon deprotection and exposure to triethylamine, these compounds rearrange into 5-aryl-2-piperidones. This approach also represents a useful route to benzazepin-2-ones unsubstituted on the nitrogen atom of the azepinone ring. |
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