Efficient Catalytic Synthesis of Condensed Isoxazole Derivatives via Intramolecular Oxidative Cycloaddition of Aldoximes

Irina A Mironova; Valentine G Nenajdenko; Pavel S Postnikov; Akio Saito; Mekhman S Yusubov; Akira Yoshimura

doi:10.3390/molecules27123860

Efficient Catalytic Synthesis of Condensed Isoxazole Derivatives via Intramolecular Oxidative Cycloaddition of Aldoximes

Molecules. 2022 Jun 16;27(12):3860. doi: 10.3390/molecules27123860.

Authors

Irina A Mironova¹, Valentine G Nenajdenko², Pavel S Postnikov¹, Akio Saito³, Mekhman S Yusubov¹, Akira Yoshimura⁴

Affiliations

¹ Research School of Chemistry and Applied Biomedical Sciences, Tomsk Polytechnic University, 634050 Tomsk, Russia.
² Department of Chemistry, M. V. Lomonosov Moscow State University, 119991 Moscow, Russia.
³ Division of Applied Chemistry, Institute of Engineering, Tokyo University of Agriculture and Technology, Tokyo 184-8588, Japan.
⁴ Faculty of Pharmaceutical Sciences, Aomori University, 2-3-1 Kobata, Aomori 030-0943, Japan.

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.

Keywords: aldoximes; catalysis; hydroxy(aryl)iodonium; hypervalent iodine; intramolecular cycloaddition; nitrogen heterocycles.

MeSH terms

Catalysis
Cycloaddition Reaction
Isoxazoles*
Oxidative Stress
Oximes*

Substances

Isoxazoles
Oximes

Abstract

MeSH terms

Substances

Grants and funding