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 Z. Zard (1)

1 DCSO - Laboratoire de synthèse organique

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

Domaines: Chimie organique

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