Wiley
Asian Journal of Organic Chemistry
,  volume 10 ,  issue 10 ,  pages 2644-2653

Ring Distortion Diversity-Oriented Approach to Fully Substituted Furoxans and Isoxazoles

Publication type: Journal Article
Publication date: 2021-09-15
Wiley
scimago Q2
wos Q2
SJR: 0.542
CiteScore: 5.0
Impact factor: 2.7
ISSN: 21935807, 21935815
Organic Chemistry
Abstract

A regioselective method for an assembly of pharmacologically relevant fully substituted furoxans and isoxazoles using the ring distortion diversity‐oriented approach through the one‐pot ring cleavage/nucleophilic addition/oxidation cascade of monosubstituted furoxans was developed. The described synthetic strategy is highly regioselective and provides single furoxan regioisomers upon utilization of N‐ or S‐nucleophiles. Utilization of the cyanide‐anion as a nucleophile in the same reaction cascade afforded a series of rather rare fully substituted isoxazoles incorporating vicinal nitro and amino functionalities. In addition, synthesized disubstituted furoxans revealed an ability to release NO indicating their strong potential as pharmacologically oriented drug candidates for various biomedical applications.

Found 
Found 
5 citations
Fershtat Leonid
DSc in Chemistry
146 publications,  2 959 citations,  121 reviews
h-index: 29
N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences
N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences
Research interests
Materials Science
Medicinal Chemistry
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4 citations
Larin Alexander
PhD in Chemistry
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h-index: 16
N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences
N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences
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Ananyev Ivan
DSc in Physics and Mathematics
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h-index: 30
Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences
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A.N.Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences
A.N.Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences
National Research University Higher School of Economics
National Research University Higher School of Economics
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Gazizov Almir
🥼
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157 publications,  879 citations,  23 reviews
h-index: 14
A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences
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Research interests
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Karasik Andrey
DSc in Chemistry, professor, associate member of the Russian Academy of Sciences 
224 publications,  2 591 citations
h-index: 26
A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences
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h-index: 22
North Caucasus Federal University
North Caucasus Federal University
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A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences
A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences
Research interests
Asymmetric metal complex catalysis
Chemistry of organic and organoelement compounds; chemistry of polymers; production of materials
Coordination chemistry of phosphorus
Organoelement chemistry
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Synthesis of chiral phosphorus-containing ligands
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Aksenov Aleksandr
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Sosnovskikh Vyacheslav
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Mendeleev University of Chemical Technology of Russia
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GOST Copy
Chaplygin D. A. et al. Ring Distortion Diversity-Oriented Approach to Fully Substituted Furoxans and Isoxazoles // Asian Journal of Organic Chemistry. 2021. Vol. 10. No. 10. pp. 2644-2653.
GOST all authors (up to 50) Copy
Chaplygin D. A., Gorbunov Y. K., Fershtat L. L. Ring Distortion Diversity-Oriented Approach to Fully Substituted Furoxans and Isoxazoles // Asian Journal of Organic Chemistry. 2021. Vol. 10. No. 10. pp. 2644-2653.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1002/ajoc.202100475
UR - https://onlinelibrary.wiley.com/doi/10.1002/ajoc.202100475
TI - Ring Distortion Diversity-Oriented Approach to Fully Substituted Furoxans and Isoxazoles
T2 - Asian Journal of Organic Chemistry
AU - Chaplygin, Daniil A
AU - Gorbunov, Yaroslav K
AU - Fershtat, Leonid L.
PY - 2021
DA - 2021/09/15
PB - Wiley
SP - 2644-2653
IS - 10
VL - 10
SN - 2193-5807
SN - 2193-5815
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2021_Chaplygin,
author = {Daniil A Chaplygin and Yaroslav K Gorbunov and Leonid L. Fershtat},
title = {Ring Distortion Diversity-Oriented Approach to Fully Substituted Furoxans and Isoxazoles},
journal = {Asian Journal of Organic Chemistry},
year = {2021},
volume = {10},
publisher = {Wiley},
month = {sep},
url = {https://onlinelibrary.wiley.com/doi/10.1002/ajoc.202100475},
number = {10},
pages = {2644--2653},
doi = {10.1002/ajoc.202100475}
}
MLA
Cite this
MLA Copy
Chaplygin, Daniil A., et al. “Ring Distortion Diversity-Oriented Approach to Fully Substituted Furoxans and Isoxazoles.” Asian Journal of Organic Chemistry, vol. 10, no. 10, Sep. 2021, pp. 2644-2653. https://onlinelibrary.wiley.com/doi/10.1002/ajoc.202100475.