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- Title
Diverse Synthesis of Fused Polyheterocyclic Compounds via [3 + 2] Cycloaddition of In Situ-Generated Heteroaromatic N -Ylides and Electron-Deficient Olefins.
- Authors
Wang, Zhen-Hua; Zhang, Tong; Shen, Li-Wen; Yang, Xiu; Zhang, Yan-Ping; You, Yong; Zhao, Jian-Qiang; Yuan, Wei-Cheng
- Abstract
[3 + 2] Cycloaddition reactions of heteroaromatic N-ylides with electron-deficient olefins have been developed. The heteroaromatic N-ylides, in situ generated from N-phenacylbenzothiazolium bromides, can smoothly react with maleimides under very mild conditions, affording fused polycyclic octahydropyrrolo[3,4-c]pyrroles in good-to-excellent isolated yields. This reaction concept could also be extended to 3-trifluoroethylidene oxindoles and benzylidenemalononitriles as electron-deficient olefins for accessing highly functionalized polyheterocyclic compounds. A gram-scale experiment was also carried out to verify the practicability of the methodology.
- Subjects
ALKENES; RING formation (Chemistry); OXINDOLES; MALEIMIDES; PYRROLES; ISOXAZOLIDINES
- Publication
Molecules, 2023, Vol 28, Issue 11, p4410
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules28114410