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Diverse Synthesis of Fused Polyheterocyclic Compounds via [3 + 2] Cycloaddition of In Situ-Generated Heteroaromatic N -Ylides and Electron-Deficient Olefins.
- Source :
-
Molecules . Jun2023, Vol. 28 Issue 11, p4410. 20p. - Publication Year :
- 2023
-
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. [ABSTRACT FROM AUTHOR]
- Subjects :
- *ALKENES
*RING formation (Chemistry)
*OXINDOLES
*MALEIMIDES
*PYRROLES
*ISOXAZOLIDINES
Subjects
Details
- Language :
- English
- ISSN :
- 14203049
- Volume :
- 28
- Issue :
- 11
- Database :
- Academic Search Index
- Journal :
- Molecules
- Publication Type :
- Academic Journal
- Accession number :
- 164216299
- Full Text :
- https://doi.org/10.3390/molecules28114410