Facile synthesis of penta-substituted pyrroles and pyrrole-fused piperidin-4-ones via four component reactions of 2,3-diketoesters, anilines and enaminones
Literature Information
Publication Date
2021-07-20
DOI
10.1039/D1QO00921D
Impact Factor
5.281
Authors
Tongyan Yu, Fei Ji, Daichuan Huang, Ya Gao, Zhaoping Shi, Xuan Sha, Jiangyan Xu, Siliang You, Mingzhi Zhang, Qiang Sha
View Original
Abstract
Given the importance of pyrroles in pharmaceuticals, agrochemicals and functional materials, the development of efficient strategies for their construction continues to be a hot area. Herein, we present a novel BF3·Et2O mediated four component reaction of 2,3-diketoesters, anilines and enaminones, providing highly functionalized pyrroles and pyrrole-fused piperidin-4-ones in moderate to good yields. The key to success lies in the utilization of enaminone as the substrate and precise capture of the carbocation intermediate by anilines, allowing the amination to occur at the 5-position smoothly. This strategy is potentially applicable to diverse nucleophilic reagents. Moreover, an intramolecular version of this strategy can be utilized to form fused heterocycles.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
![(2S)-2-({N-[(2S)-2-Ammonio-4-methylpentanoyl]glycyl}amino)-3-phenylpropanoate structure](https://static.chemtradehub.com/structs/429/4294-25-1-0842.webp "(2S)-2-({N-[(2S)-2-Ammonio-4-methylpentanoyl]glycyl}amino)-3-phenylpropanoate structure")
(2S)-2-({N-[(2S)-2-Ammonio-4-methylpentanoyl]glycyl}amino)-3-phenylpropanoate
CAS Number:
4294-25-1
Molecular Formula:
C17H25N3O4
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