Synthesis of functionalized indolizines through 1,3-dipolar cycloaddition of zwitterionic ketenimines and pyridinium salts
A straightforward and efficient strategy for the synthesis of fully functionalized indolizines has been developed through a transition metal- and oxidant-free [3 + 2] cycloaddition reaction of zwitterionic ketenimines and pyridinium salts. This versatile method proceeds under mild conditions, afford...
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| Hauptverfasser: | , , , |
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| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
2 May 2025
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| In: |
The journal of organic chemistry
Year: 2025, Jahrgang: 90, Heft: 17, Pages: 5973-5985 |
| ISSN: | 1520-6904 |
| DOI: | 10.1021/acs.joc.5c00295 |
| Online-Zugang: | Verlag, kostenfrei, Volltext: https://doi.org/10.1021/acs.joc.5c00295
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| Verfasserangaben: | Farhad Golmohammadi, Chiman Osmani, Frank Rominger, and Saeed Balalaie |
| Zusammenfassung: | A straightforward and efficient strategy for the synthesis of fully functionalized indolizines has been developed through a transition metal- and oxidant-free [3 + 2] cycloaddition reaction of zwitterionic ketenimines and pyridinium salts. This versatile method proceeds under mild conditions, affording functionalized indolizines in moderate to good yields. This efficient approach involves an intermolecular [3 + 2] cycloaddition, followed by enamine/imine tautomerization and aromatization. Notably, this method demonstrates broad functional group compatibility and allows for facile scalability, making it a valuable tool for the synthesis of indolizine-based frameworks in organic and medicinal chemistry. |
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| Beschreibung: | Online veröffentlicht: 19. April 2025 Gesehen am 29.09.2025 |
| Beschreibung: | Online Resource |
| ISSN: | 1520-6904 |
| DOI: | 10.1021/acs.joc.5c00295 |