Desulfonylative radical ring closure onto aromatics. A modular route to benzazepin-2-ones and 5-arylpiperidin-2-ones
| Autor: | Nicolas Charrier, Samir Z. Zard, Zhibo Liu |
|---|---|
| Přispěvatelé: | Laboratoire de synthèse organique (DCSO), École polytechnique (X)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS) |
| Jazyk: | angličtina |
| Rok vydání: | 2012 |
| Předmět: |
Molecular Structure
Nitrogen 010405 organic chemistry [CHIM.ORGA]Chemical Sciences/Organic chemistry Organic Chemistry Intermolecular force Closure (topology) Benzazepines 010402 general chemistry Ring (chemistry) 01 natural sciences Biochemistry Catalysis Allylamine 0104 chemical sciences Adduct chemistry.chemical_compound chemistry Nitrogen atom Cyclization Polymer chemistry Physical and Theoretical Chemistry Triethylamine Piperidones |
| Zdroj: | Organic Letters Organic Letters, American Chemical Society, 2012, 14 (8), pp.2018-2021. ⟨10.1021/ol3005276⟩ |
| ISSN: | 1523-7060 1523-7052 |
| Popis: | International audience; 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 |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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