An Oxidative [3+2+1] Cyclization of Enaminones and N‐Alkenyl‐2‐pyrrolidinone: Access to Polysubstituted 4‐Alkylated 1,4‐dihydropyridines

An oxidative [3+2+1] cyclization of enaminones and N‐alkenyl‐2‐pyrrolidinone is described for the synthesis of 4‐alkylated 1,4‐dihydropyridines (1,4‐DHPs). By using terminal olefin as the C4 source of the 1,4‐DHP skeleton, this synthetic strategy provides a series of 1,4‐DHPs through a 1,1‐difunctio...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2023-04, Vol.365 (8), p.1217-1223
Main Authors: Chai, Zhangmengjie, Chen, Longkun, Liu, Zhuoyuan, Sun, Yulin, Liu, Donghan, Zhang, Mingshuai, Wang, Yongchao, Yu, Fuchao
Format: Article
Language:English
Subjects:
4-Alkylated 1,4-dihydropyridines
Alkylation
Enaminones
N-Alkenyl-2-pyrrolidinone
Oxidative [3+2+1] cyclization
Terminal olefin
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Summary:An oxidative [3+2+1] cyclization of enaminones and N‐alkenyl‐2‐pyrrolidinone is described for the synthesis of 4‐alkylated 1,4‐dihydropyridines (1,4‐DHPs). By using terminal olefin as the C4 source of the 1,4‐DHP skeleton, this synthetic strategy provides a series of 1,4‐DHPs through a 1,1‐difunctionalization/cyclization process. In this protocol, two C(sp3)−C(sp2) bonds and a C(sp2)−N bond are simultaneously formed, the hydrogen source on the newly formed methyl group of the 1,4‐DHP skeleton is confirmed and a possible mechanism is proposed.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202300088