Access to thiionized-, selenolized-, and alkylated 5-alkylidene 3-pyrrolin-2-one derivatives a regioselective oxidative annulation reaction

A metal-free regioselective oxidative annulation reaction of readily available 2,4-pentanediones with primary amines has been described. This protocol provides a divergent strategy for the incorporation of various radical donors into 5-alkylidene 3-pyrrolin-2-one skeletons, producing a variety of th...

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Published in:Organic & biomolecular chemistry 2023-03, Vol.21 (12), p.2596-262
Main Authors: Liu, Donghan, Song, Siyu, Chen, Longkun, Zhang, Mingshuai, Liu, Zhuoyuan, Lu, Xihang, Huang, Jiuzhong, Yu, Fuchao
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Summary:A metal-free regioselective oxidative annulation reaction of readily available 2,4-pentanediones with primary amines has been described. This protocol provides a divergent strategy for the incorporation of various radical donors into 5-alkylidene 3-pyrrolin-2-one skeletons, producing a variety of thiionized-, selenolized-, and alkylated 5-alkylidene 3-pyrrolin-2-one derivatives. Moreover, the diverse synthetic transformations of the 5-alkylidene 3-pyrrolin-2-one products were also investigated. Polyfunctional thiionized-, selenolized-, and alkylated 5-alkylidene 3-pyrrolin-2-one derivatives are easily constructed via a metal-free regioselective oxidative annulation reaction.
ISSN:1477-0520
1477-0539
DOI:10.1039/d3ob00014a