Domino Approach for the Synthesis of Pyridinium Salts and 1,2,3,8a-Tetrahydroimidazo[1,2-a]pyridines from 2-Imidazolines and Propiolic Acid Esters
Publication type: Journal Article
Publication date: 2023-07-26
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
37494140
Organic Chemistry
Abstract
Adducts of 1-alkyl-2-imidazolines and two molecules of alkyl propiolate, possessing an N-propargyl-β-enaminoester fragment, easily undergo a domino reaction to form pyridinium salts with β-(alkylammonio)ethyl group at the nitrogen atom in the presence of 2 equiv of a protic acid. Treatment of the above reaction mixture with a base gives 1,2,3,8a-tetrahydroimidazo[1,2-a]pyridines. Reaction of the latter compounds with acid chlorides affords pyridinium salts with β-(alkylamido)ethyl moiety at the nitrogen atom.
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Golantsov N. E. et al. Domino Approach for the Synthesis of Pyridinium Salts and 1,2,3,8a-Tetrahydroimidazo[1,2-a]pyridines from 2-Imidazolines and Propiolic Acid Esters // Journal of Organic Chemistry. 2023. Vol. 88. No. 16. pp. 11603-11617.
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Golantsov N. E., Golubenkova A. S., Festa A. A., Novikov A. P., Varlamov A. V., Voskressensky L. G. Domino Approach for the Synthesis of Pyridinium Salts and 1,2,3,8a-Tetrahydroimidazo[1,2-a]pyridines from 2-Imidazolines and Propiolic Acid Esters // Journal of Organic Chemistry. 2023. Vol. 88. No. 16. pp. 11603-11617.
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TY - JOUR
DO - 10.1021/acs.joc.3c00916
UR - https://pubs.acs.org/doi/10.1021/acs.joc.3c00916
TI - Domino Approach for the Synthesis of Pyridinium Salts and 1,2,3,8a-Tetrahydroimidazo[1,2-a]pyridines from 2-Imidazolines and Propiolic Acid Esters
T2 - Journal of Organic Chemistry
AU - Golantsov, Nikita E
AU - Golubenkova, Alexandra S.
AU - Festa, Alexey A.
AU - Novikov, Anton P.
AU - Varlamov, Alexey V.
AU - Voskressensky, Leonid G.
PY - 2023
DA - 2023/07/26
PB - American Chemical Society (ACS)
SP - 11603-11617
IS - 16
VL - 88
PMID - 37494140
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2023_Golantsov,
author = {Nikita E Golantsov and Alexandra S. Golubenkova and Alexey A. Festa and Anton P. Novikov and Alexey V. Varlamov and Leonid G. Voskressensky},
title = {Domino Approach for the Synthesis of Pyridinium Salts and 1,2,3,8a-Tetrahydroimidazo[1,2-a]pyridines from 2-Imidazolines and Propiolic Acid Esters},
journal = {Journal of Organic Chemistry},
year = {2023},
volume = {88},
publisher = {American Chemical Society (ACS)},
month = {jul},
url = {https://pubs.acs.org/doi/10.1021/acs.joc.3c00916},
number = {16},
pages = {11603--11617},
doi = {10.1021/acs.joc.3c00916}
}
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MLA
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Golantsov, Nikita E., et al. “Domino Approach for the Synthesis of Pyridinium Salts and 1,2,3,8a-Tetrahydroimidazo[1,2-a]pyridines from 2-Imidazolines and Propiolic Acid Esters.” Journal of Organic Chemistry, vol. 88, no. 16, Jul. 2023, pp. 11603-11617. https://pubs.acs.org/doi/10.1021/acs.joc.3c00916.