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Acid-Switchable Synthesis of Trifluoromethylated Triazoles and Isoxazoles via Reaction of CF3-Ynones with NaN3: DFT Study of the Reaction Mechanism
Publication type: Journal Article
Publication date: 2022-11-22
scimago Q1
wos Q1
SJR: 1.273
CiteScore: 9.0
Impact factor: 4.9
ISSN: 16616596, 14220067
PubMed ID:
36498860
Catalysis
Organic Chemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Computer Science Applications
Spectroscopy
Molecular Biology
General Medicine
Abstract
A detailed study of the reaction of CF3-ynones with NaN3 was performed. It was found that the reaction permits the selective synthesis of either 4-trifluoroacetyltriazoles or 5-CF3-isoxazoles. The chemoselectivity of the reaction was switchable via acid catalysis. The reaction of CF3-ynones with NaN3 in EtOH produced high yields of 4-trifluoroacetyltriazoles. In contrast, the formation of 5-CF3-isoxazoles was observed under catalysis by acids. This acid-switchable procedure can be performed at sub-gram scale. The possible reaction mechanism was supported by DFT calculations. The synthetic utility of the prepared 4-trifluoroacetyltriazoles was demonstrated.
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8
Total citations:
8
Citations from 2024:
5
(62.5%)
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Muzalevskiy V. M. et al. Acid-Switchable Synthesis of Trifluoromethylated Triazoles and Isoxazoles via Reaction of CF3-Ynones with NaN3: DFT Study of the Reaction Mechanism // International Journal of Molecular Sciences. 2022. Vol. 23. No. 23. p. 14522.
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Muzalevskiy V. M., Sizova Z. A., Nechaev M. S., Nenajdenko V. G. Acid-Switchable Synthesis of Trifluoromethylated Triazoles and Isoxazoles via Reaction of CF3-Ynones with NaN3: DFT Study of the Reaction Mechanism // International Journal of Molecular Sciences. 2022. Vol. 23. No. 23. p. 14522.
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RIS
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TY - JOUR
DO - 10.3390/ijms232314522
UR - https://doi.org/10.3390/ijms232314522
TI - Acid-Switchable Synthesis of Trifluoromethylated Triazoles and Isoxazoles via Reaction of CF3-Ynones with NaN3: DFT Study of the Reaction Mechanism
T2 - International Journal of Molecular Sciences
AU - Muzalevskiy, Vasiliy M
AU - Sizova, Zoia A
AU - Nechaev, Mikhail. S.
AU - Nenajdenko, Valentine G.
PY - 2022
DA - 2022/11/22
PB - MDPI
SP - 14522
IS - 23
VL - 23
PMID - 36498860
SN - 1661-6596
SN - 1422-0067
ER -
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BibTex (up to 50 authors)
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@article{2022_Muzalevskiy,
author = {Vasiliy M Muzalevskiy and Zoia A Sizova and Mikhail. S. Nechaev and Valentine G. Nenajdenko},
title = {Acid-Switchable Synthesis of Trifluoromethylated Triazoles and Isoxazoles via Reaction of CF3-Ynones with NaN3: DFT Study of the Reaction Mechanism},
journal = {International Journal of Molecular Sciences},
year = {2022},
volume = {23},
publisher = {MDPI},
month = {nov},
url = {https://doi.org/10.3390/ijms232314522},
number = {23},
pages = {14522},
doi = {10.3390/ijms232314522}
}
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MLA
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Muzalevskiy, Vasiliy M., et al. “Acid-Switchable Synthesis of Trifluoromethylated Triazoles and Isoxazoles via Reaction of CF3-Ynones with NaN3: DFT Study of the Reaction Mechanism.” International Journal of Molecular Sciences, vol. 23, no. 23, Nov. 2022, p. 14522. https://doi.org/10.3390/ijms232314522.
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