Open Access
Efficient Catalytic Synthesis of Condensed Isoxazole Derivatives via Intramolecular Oxidative Cycloaddition of Aldoximes
Irina A. Mironova
1
,
Akio Saito
3
,
4
Faculty of Pharmaceutical Sciences, Aomori University, 2-3-1 Kobata, Aomori 030-0943, Japan
|
Publication type: Journal Article
Publication date: 2022-06-16
PubMed ID:
35744982
Organic Chemistry
Drug Discovery
Physical and Theoretical Chemistry
Pharmaceutical Science
Molecular Medicine
Analytical Chemistry
Chemistry (miscellaneous)
Abstract
The intramolecular oxidative cycloaddition reaction of alkyne- or alkene-tethered aldoximes was catalyzed efficiently by hypervalent iodine(III) species to afford the corresponding polycyclic isoxazole derivatives in up to a 94% yield. The structure of the prepared products was confirmed by various methods, including X-ray crystallography. Mechanistic study demonstrated the crucial role of hydroxy(aryl)iodonium tosylate as a precatalyst, which is generated from 2-iodobenzoic acid and m-chloroperoxybenzoic acid in the presence of a catalytic amount of p-toluenesulfonic acid.
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11
Total citations:
11
Citations from 2024:
6
(54%)
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MLA
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GOST
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Mironova I. A. et al. Efficient Catalytic Synthesis of Condensed Isoxazole Derivatives via Intramolecular Oxidative Cycloaddition of Aldoximes // Molecules. 2022. Vol. 27. No. 12. p. 3860.
GOST all authors (up to 50)
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Mironova I. A., Nenajdenko V. G., Postnikov P. S., Saito A., S. Yusubov M., YOSHIMURA A. Efficient Catalytic Synthesis of Condensed Isoxazole Derivatives via Intramolecular Oxidative Cycloaddition of Aldoximes // Molecules. 2022. Vol. 27. No. 12. p. 3860.
Cite this
RIS
Copy
TY - JOUR
DO - 10.3390/molecules27123860
UR - https://www.mdpi.com/1420-3049/27/12/3860
TI - Efficient Catalytic Synthesis of Condensed Isoxazole Derivatives via Intramolecular Oxidative Cycloaddition of Aldoximes
T2 - Molecules
AU - Mironova, Irina A.
AU - Nenajdenko, Valentine G.
AU - Postnikov, Pavel S.
AU - Saito, Akio
AU - S. Yusubov, Mekhman
AU - YOSHIMURA, Akira
PY - 2022
DA - 2022/06/16
PB - MDPI
SP - 3860
IS - 12
VL - 27
PMID - 35744982
SN - 1420-3049
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2022_Mironova,
author = {Irina A. Mironova and Valentine G. Nenajdenko and Pavel S. Postnikov and Akio Saito and Mekhman S. Yusubov and Akira YOSHIMURA},
title = {Efficient Catalytic Synthesis of Condensed Isoxazole Derivatives via Intramolecular Oxidative Cycloaddition of Aldoximes},
journal = {Molecules},
year = {2022},
volume = {27},
publisher = {MDPI},
month = {jun},
url = {https://www.mdpi.com/1420-3049/27/12/3860},
number = {12},
pages = {3860},
doi = {10.3390/molecules27123860}
}
Cite this
MLA
Copy
Mironova, Irina A., et al. “Efficient Catalytic Synthesis of Condensed Isoxazole Derivatives via Intramolecular Oxidative Cycloaddition of Aldoximes.” Molecules, vol. 27, no. 12, Jun. 2022, p. 3860. https://www.mdpi.com/1420-3049/27/12/3860.