Facile synthesis of penta-substituted pyrroles and pyrrole-fused piperidin-4-ones via four component reactions of 2,3-diketoesters, anilines and enaminones

文献情報

出版日 2021-07-20

DOI 10.1039/D1QO00921D

インパクトファクター 5.281

著者

Tongyan Yu, Fei Ji, Daichuan Huang, Ya Gao, Zhaoping Shi, Xuan Sha, Jiangyan Xu, Siliang You, Mingzhi Zhang, Qiang Sha

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要旨

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.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 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

Facile synthesis of penta-substituted pyrroles and pyrrole-fused piperidin-4-ones via four component reactions of 2,3-diketoesters, anilines and enaminones

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