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.

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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

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article

Synthesis of Functionalized Indolizines through 1,3-Dipolar Cycloaddition of Zwitterionic Ketenimines and Pyridinium Salts

Saeed Balalaie, Chiman Osmani, Farhad Golmohammadi, Frank Röminger
6 citations
The Journal of Organic Chemistry
Synthesis and Reactivity of Heterocycles
5.62
article

Synthesis of Functionalized Indolizines through 1,3-Dipolar Cycloaddition of Zwitterionic Ketenimines and Pyridinium Salts

Saeed Balalaie, Chiman Osmani, Farhad Golmohammadi, Frank Röminger
article en
6 citations

Abstract

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.

The Journal of Organic ChemistryVol. 90(17)
Heidelberg University (DE), K. N. Toosi University of Technology (IR)
Alexander von Humboldt-Stiftung, Iran National Science Foundation
Openalex Percentile: Top 4%
Synthesis and Reactivity of Heterocycles
5.62
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