Open Access
Regioselective Synthesis of NO-Donor (4-Nitro-1,2,3-triazolyl)furoxans via Eliminative Azide–Olefin Cycloaddition
Publication type: Journal Article
Publication date: 2023-10-07
PubMed ID:
37836813
Organic Chemistry
Drug Discovery
Physical and Theoretical Chemistry
Pharmaceutical Science
Molecular Medicine
Analytical Chemistry
Chemistry (miscellaneous)
Abstract
A facile and efficient method for the regioselective [3 + 2] cycloaddition of 4-azidofuroxans to 1-dimethylamino-2-nitroethylene under p-TSA catalysis affording (4-nitro-1,2,3-triazolyl)furoxans was developed. This transformation is believed to proceed via eliminative azide–olefin cycloaddition resulting in its complete regioselectivity. The developed protocol has a broad substrate scope and enables a straightforward assembly of the 4-nitro-1,2,3-triazole motif. Moreover, synthesized (4-nitro-1,2,3-triazolyl)furoxans were found to be capable of NO release in a broad range of concentrations, thus providing a novel platform for future drug design and related biomedical applications of heterocyclic NO donors.
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Stebletsova I. A. et al. Regioselective Synthesis of NO-Donor (4-Nitro-1,2,3-triazolyl)furoxans via Eliminative Azide–Olefin Cycloaddition // Molecules. 2023. Vol. 28. No. 19. p. 6969.
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Stebletsova I. A., Larin A. A., Ananyev I. V., Fershtat L. L. Regioselective Synthesis of NO-Donor (4-Nitro-1,2,3-triazolyl)furoxans via Eliminative Azide–Olefin Cycloaddition // Molecules. 2023. Vol. 28. No. 19. p. 6969.
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RIS
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TY - JOUR
DO - 10.3390/molecules28196969
UR - https://www.mdpi.com/1420-3049/28/19/6969
TI - Regioselective Synthesis of NO-Donor (4-Nitro-1,2,3-triazolyl)furoxans via Eliminative Azide–Olefin Cycloaddition
T2 - Molecules
AU - Stebletsova, Irina A.
AU - Larin, Alexander A
AU - Ananyev, Ivan V
AU - Fershtat, Leonid L.
PY - 2023
DA - 2023/10/07
PB - MDPI
SP - 6969
IS - 19
VL - 28
PMID - 37836813
SN - 1420-3049
ER -
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BibTex (up to 50 authors)
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@article{2023_Stebletsova,
author = {Irina A. Stebletsova and Alexander A Larin and Ivan V Ananyev and Leonid L. Fershtat},
title = {Regioselective Synthesis of NO-Donor (4-Nitro-1,2,3-triazolyl)furoxans via Eliminative Azide–Olefin Cycloaddition},
journal = {Molecules},
year = {2023},
volume = {28},
publisher = {MDPI},
month = {oct},
url = {https://www.mdpi.com/1420-3049/28/19/6969},
number = {19},
pages = {6969},
doi = {10.3390/molecules28196969}
}
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MLA
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Stebletsova, Irina A., et al. “Regioselective Synthesis of NO-Donor (4-Nitro-1,2,3-triazolyl)furoxans via Eliminative Azide–Olefin Cycloaddition.” Molecules, vol. 28, no. 19, Oct. 2023, p. 6969. https://www.mdpi.com/1420-3049/28/19/6969.