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- Title
Efficient Catalytic Synthesis of Condensed Isoxazole Derivatives via Intramolecular Oxidative Cycloaddition of Aldoximes.
- Authors
Mironova, Irina A.; Nenajdenko, Valentine G.; Postnikov, Pavel S.; Saito, Akio; Yusubov, Mekhman S.; Yoshimura, Akira
- 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.
- Subjects
RING formation (Chemistry); ISOXAZOLES; ALDOXIMES; X-ray crystallography; IODINE
- Publication
Molecules, 2022, Vol 27, Issue 12, p3860
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules27123860