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- Title
Dipolarophile-Controlled Regioselective 1,3-Dipolar Cycloaddition: A Switchable Divergent Access to Functionalized N -Fused Pyrrolidinyl Spirooxindoles.
- Authors
Wang, Yongchao; Yan, Lijun; Yan, Yuxin; Li, Sujin; Lu, Hongying; Liu, Jia; Dong, Jianwei
- Abstract
N-fused pyrrolidinyl spirooxindole belongs to a class of privileged heterocyclic scaffolds and is prevalent in natural alkaloids and synthetic pharmaceutical molecules. To realize the switchable synthesis of divergent N-fused pyrrolidinyl spirooxindoles for further biological activity evaluation via a substrate-controlled strategy, a chemically sustainable, catalysis-free, and dipolarophile-controlled three-component 1,3-dipolar cycloaddition of isatin-derived azomethine ylides with diverse dipolarophiles is described in this work. A total of 40 functionalized N-fused pyrrolidinyl spirooxindoles were synthesized in 76–95% yields with excellent diastereoselectivities (up to >99:1 dr). The scaffolds of these products can be well-controlled by employing different 1,4-enedione derivatives as dipolarophiles in EtOH at room temperature. This study provides an efficient strategy to afford a spectrum of natural-like and potentially bioactive N-fused pyrrolidinyl spirooxindoles.
- Subjects
RING formation (Chemistry); YLIDES; MOLECULES
- Publication
International Journal of Molecular Sciences, 2023, Vol 24, Issue 4, p3771
- ISSN
1661-6596
- Publication type
Article
- DOI
10.3390/ijms24043771