Desulfonylative radical ring closure onto aromatics. A modular route to benzazepin-2-ones and 5-arylpiperidin-2-ones.

Nicolas Charrier 1 Zhibo Liu 1 Samir Zard 1, *
* Corresponding author
1 DCSO - Laboratoire de synthèse organique
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. © 2012 American Chemical Society
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Submitted on : Tuesday, February 25, 2014 - 12:29:49 PM
Last modification on : Thursday, February 7, 2019 - 5:16:34 PM

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Nicolas Charrier, Zhibo Liu, Samir Zard. Desulfonylative radical ring closure onto aromatics. A modular route to benzazepin-2-ones and 5-arylpiperidin-2-ones.. Organic Letters, American Chemical Society, 2012, 14 (8), pp.2018-2021. ⟨10.1021/ol3005276⟩. ⟨hal-00949983⟩

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