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

Nicolas Charrier; Zhibo Liu; Samir Zard

doi:10.1021/ol3005276

Journal articles

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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Journal articles

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Chemical Sciences / Organic chemistry

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

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