Journal of Organic Chemistry, volume 87, issue 9, pages 6514-6519
Synthesis of Imidazo[1,2- a]pyridines via Near UV Light-Induced Cyclization of Azirinylpyridinium Salts
Publication type: Journal Article
Publication date: 2022-04-27
Journal:
Journal of Organic Chemistry
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 3.6
ISSN: 00223263, 15206904
Organic Chemistry
Abstract
An efficient one-pot synthesis of imidazo[1,2-a]pyridines from 2-bromoazirines and pyridines has been developed. The construction of the bicyclic framework of imidazo[1,2-a]pyridines occurs in two steps through the formation of (2H-azirin-2-yl)pyridinium bromides followed by dehydrobrominative UV light-induced cyclization. The method can also be applied for the synthesis of imidazo[2,1-a]isoquinolines. Unstable in solution, (2H-azirin-2-yl)pyridinium/isoquinolinium bromides were quantitatively converted to stable tetrafluoroborates, which can be cyclized to imidazo[1,2-a]pyridines under UV irradiation in the presence of bromide ions.
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Citations by publishers
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Filippov I. P. et al. Synthesis of Imidazo[1,2- a]pyridines via Near UV Light-Induced Cyclization of Azirinylpyridinium Salts // Journal of Organic Chemistry. 2022. Vol. 87. No. 9. pp. 6514-6519.
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Filippov I. P., Agafonova A. V., Titov G. D., Smetanin I. A., Rostovskii N. V., Khlebnikov A. F., Novikov M. S. Synthesis of Imidazo[1,2- a]pyridines via Near UV Light-Induced Cyclization of Azirinylpyridinium Salts // Journal of Organic Chemistry. 2022. Vol. 87. No. 9. pp. 6514-6519.
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TY - JOUR
DO - 10.1021/acs.joc.2c00514
UR - https://doi.org/10.1021%2Facs.joc.2c00514
TI - Synthesis of Imidazo[1,2- a]pyridines via Near UV Light-Induced Cyclization of Azirinylpyridinium Salts
T2 - Journal of Organic Chemistry
AU - Filippov, Ilya P
AU - Agafonova, Anastasiya V
AU - Smetanin, Ilia A
AU - Titov, Gleb D
AU - Rostovskii, Nikolai V
AU - Khlebnikov, Alexander F
AU - Novikov, Mikhail S.
PY - 2022
DA - 2022/04/27 00:00:00
PB - American Chemical Society (ACS)
SP - 6514-6519
IS - 9
VL - 87
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2022_Filippov,
author = {Ilya P Filippov and Anastasiya V Agafonova and Ilia A Smetanin and Gleb D Titov and Nikolai V Rostovskii and Alexander F Khlebnikov and Mikhail S. Novikov},
title = {Synthesis of Imidazo[1,2- a]pyridines via Near UV Light-Induced Cyclization of Azirinylpyridinium Salts},
journal = {Journal of Organic Chemistry},
year = {2022},
volume = {87},
publisher = {American Chemical Society (ACS)},
month = {apr},
url = {https://doi.org/10.1021%2Facs.joc.2c00514},
number = {9},
pages = {6514--6519},
doi = {10.1021/acs.joc.2c00514}
}
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MLA
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Filippov, Ilya P., et al. “Synthesis of Imidazo[1,2- a]pyridines via Near UV Light-Induced Cyclization of Azirinylpyridinium Salts.” Journal of Organic Chemistry, vol. 87, no. 9, Apr. 2022, pp. 6514-6519. https://doi.org/10.1021%2Facs.joc.2c00514.