Zinc‐Mediated Carbamoyl Amination of Alkylidenecyclopropane‐Tethered Carbamoyl Chlorides: Synthesis of Functionalized 2‐Quinolones

The transition metal catalyzed cyclization of alkene‐tethered carbamoyl chloride has emerged as a tool to construct oxindoles bearing quaternary centers. Most of these reactions proceed via carbometalation‐initiated 5‐exo‐trig cyclization followed by nucleophilic trapping of the resulting σ alkyl‐me...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2024-11, Vol.366 (22), p.4644-4648
Main Authors: Deng, Jing‐Tong, Lang, Ming, Peng, Jin‐Bao
Format: Article
Language:English
Subjects:
2-quinolones
ACP-tethered
Alkenes
Aniline
Carbamoyl amination
Carbamoyl chlorides
Chemical reactions
Chemical synthesis
Chlorides
Transition metals
Zinc
Zn-mediated
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Summary:The transition metal catalyzed cyclization of alkene‐tethered carbamoyl chloride has emerged as a tool to construct oxindoles bearing quaternary centers. Most of these reactions proceed via carbometalation‐initiated 5‐exo‐trig cyclization followed by nucleophilic trapping of the resulting σ alkyl‐metal species to achieve diverse functionalized oxindoles. The 6‐endo‐trig type cyclization of alkene‐tethered carbamoyl chloride has been rarely reported. Herein, a zinc‐mediated carbamoyl amination of alkylidenecyclopropane‐tethered carbamoyl chlorides with anilines for the synthesis of functionalized 2‐quinolones was developed. A range of different substituted 2‐quinolones were prepared in 65–89% yield from alkylidenecyclopropane‐tethered carbamoyl chlorides and aniline derivatives using a Zn/TMSCl system.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202400849