Access to pyrrolines and fused diaziridines by selective radical addition to homoallylic diazirines‡
Literature Information
Publication Date
2023-12-29
DOI
10.1039/D3SC04886A
Impact Factor
9.825
Authors
Zhigang Ma, Xinxin Wu, Haotian Li, Zhu Cao
View Original
Abstract
Pyrroline derivatives are common in bioactive natural products and therapeutic agents. We report here a synthesis of pyrrolines and fused diaziridines by divergent radical cyclization of homoallylic diazirines, which can serve as an internal radical trap and a nitrogen source. This reaction proceeds by selective radical addition to CC or NN bonds followed by intramolecular cyclization. Frontier molecular orbital analysis provides a deep insight into the origin of the selectivity. The reaction demonstrates a new cyclization mode, broad functional group compatibility and high product diversity, and reveals a much broader chemical space for diazirine studies.
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Source Journal
Chemical Science
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Recommended Compounds
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19-[Chloro(dideuterio)methyl]-19-deuterio-20,20-dideuteriooxyoctatriacontane-18,21-dione
CAS Number:
1246818-85-8
Molecular Formula:
C39H75ClO4
![2-[(E)-(2-Methoxyphenyl)diazenyl]-3-oxo-N-(2-oxo-2,3-dihydro-1H-benzimidazol-5-yl)butanamide structure](https://static.chemtradehub.com/structs/821/82199-12-0-f1d0.webp "2-[(E)-(2-Methoxyphenyl)diazenyl]-3-oxo-N-(2-oxo-2,3-dihydro-1H-benzimidazol-5-yl)butanamide structure")
2-[(E)-(2-Methoxyphenyl)diazenyl]-3-oxo-N-(2-oxo-2,3-dihydro-1H-benzimidazol-5-yl)butanamide
CAS Number:
82199-12-0
Molecular Formula:
C18H17N5O4
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