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, 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.
Authors
- Saeed Balalaie (ORCID: https://orcid.org/0000-0002-5764-0442)
- Chiman Osmani (ORCID: https://orcid.org/0000-0002-7767-739X)
- Farhad Golmohammadi (ORCID: https://orcid.org/0000-0003-1658-0401)
- Frank Röminger
Institutions
- Heidelberg University (DE)
- K. N. Toosi University of Technology (IR)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-04-19
- DOI
- https://doi.org/10.1021/acs.joc.5c00295
- Citations
- 6
- Primary Topic
- Synthesis and Reactivity of Heterocycles
- Type
- article
- Field-Weighted Citation Impact
- 5.62
Funders
- Alexander von Humboldt-Stiftung
- Iran National Science Foundation