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

Nicolas Charrier; Zhibo Liu; Samir Zard

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

Document type :

Journal articles

Domain :

Chemical Sciences / Organic chemistry

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https://hal-polytechnique.archives-ouvertes.fr/hal-00949983
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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

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

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

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