volume 90 issue 17 pages 5973-5985

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

Farhad Golmohammadi 1, 2
Chiman Osmani 1, 2
Frank Rominger 3
Saeed Balalaie 1, 2, 4, 5
1
 
Peptide Chemistry Research Institute, Tehran, Iran
4
 
Peptide Chemistry Research Institute
5
 
K. N. Toosi University of Technology
Publication typeJournal Article
Publication date2025-04-19
scimago Q2
wos Q1
SJR0.737
CiteScore6.1
Impact factor3.6
ISSN00223263, 15206904
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.
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Golmohammadi F. et al. Synthesis of Functionalized Indolizines through 1,3-Dipolar Cycloaddition of Zwitterionic Ketenimines and Pyridinium Salts // Journal of Organic Chemistry. 2025. Vol. 90. No. 17. pp. 5973-5985.
GOST all authors (up to 50) Copy
Golmohammadi F., Osmani C., Rominger F., Balalaie S. Synthesis of Functionalized Indolizines through 1,3-Dipolar Cycloaddition of Zwitterionic Ketenimines and Pyridinium Salts // Journal of Organic Chemistry. 2025. Vol. 90. No. 17. pp. 5973-5985.
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TY - JOUR
DO - 10.1021/acs.joc.5c00295
UR - https://pubs.acs.org/doi/10.1021/acs.joc.5c00295
TI - Synthesis of Functionalized Indolizines through 1,3-Dipolar Cycloaddition of Zwitterionic Ketenimines and Pyridinium Salts
T2 - Journal of Organic Chemistry
AU - Golmohammadi, Farhad
AU - Osmani, Chiman
AU - Rominger, Frank
AU - Balalaie, Saeed
PY - 2025
DA - 2025/04/19
PB - American Chemical Society (ACS)
SP - 5973-5985
IS - 17
VL - 90
SN - 0022-3263
SN - 1520-6904
ER -
BibTex |
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BibTex (up to 50 authors) Copy
@article{2025_Golmohammadi,
author = {Farhad Golmohammadi and Chiman Osmani and Frank Rominger and Saeed Balalaie},
title = {Synthesis of Functionalized Indolizines through 1,3-Dipolar Cycloaddition of Zwitterionic Ketenimines and Pyridinium Salts},
journal = {Journal of Organic Chemistry},
year = {2025},
volume = {90},
publisher = {American Chemical Society (ACS)},
month = {apr},
url = {https://pubs.acs.org/doi/10.1021/acs.joc.5c00295},
number = {17},
pages = {5973--5985},
doi = {10.1021/acs.joc.5c00295}
}
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Golmohammadi, Farhad, et al. “Synthesis of Functionalized Indolizines through 1,3-Dipolar Cycloaddition of Zwitterionic Ketenimines and Pyridinium Salts.” Journal of Organic Chemistry, vol. 90, no. 17, Apr. 2025, pp. 5973-5985. https://pubs.acs.org/doi/10.1021/acs.joc.5c00295.
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