Efficient Catalytic Synthesis of Condensed Isoxazole Derivatives via Intramolecular Oxidative Cycloaddition of Aldoximes
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...
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| Format: | Article |
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MDPI AG
2022-06-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/12/3860 |
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| author | Irina A. Mironova Valentine G. Nenajdenko Pavel S. Postnikov Akio Saito Mekhman S. Yusubov Akira Yoshimura |
| author_facet | Irina A. Mironova Valentine G. Nenajdenko Pavel S. Postnikov Akio Saito Mekhman S. Yusubov Akira Yoshimura |
| author_sort | Irina A. Mironova |
| collection | DOAJ |
| description | 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 <i>m</i>-chloroperoxybenzoic acid in the presence of a catalytic amount of <i>p</i>-toluenesulfonic acid. |
| first_indexed | 2024-03-09T22:55:15Z |
| format | Article |
| id | doaj.art-8df83dc7452546dd950d2f27695616c7 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T22:55:15Z |
| publishDate | 2022-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-8df83dc7452546dd950d2f27695616c72023-11-23T18:12:38ZengMDPI AGMolecules1420-30492022-06-012712386010.3390/molecules27123860Efficient Catalytic Synthesis of Condensed Isoxazole Derivatives via Intramolecular Oxidative Cycloaddition of AldoximesIrina A. Mironova0Valentine G. Nenajdenko1Pavel S. Postnikov2Akio Saito3Mekhman S. Yusubov4Akira Yoshimura5Research School of Chemistry and Applied Biomedical Sciences, Tomsk Polytechnic University, 634050 Tomsk, RussiaDepartment of Chemistry, M. V. Lomonosov Moscow State University, 119991 Moscow, RussiaResearch School of Chemistry and Applied Biomedical Sciences, Tomsk Polytechnic University, 634050 Tomsk, RussiaDivision of Applied Chemistry, Institute of Engineering, Tokyo University of Agriculture and Technology, Tokyo 184-8588, JapanResearch School of Chemistry and Applied Biomedical Sciences, Tomsk Polytechnic University, 634050 Tomsk, RussiaFaculty of Pharmaceutical Sciences, Aomori University, 2-3-1 Kobata, Aomori 030-0943, JapanThe 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 <i>m</i>-chloroperoxybenzoic acid in the presence of a catalytic amount of <i>p</i>-toluenesulfonic acid.https://www.mdpi.com/1420-3049/27/12/3860hypervalent iodinehydroxy(aryl)iodoniumcatalysisaldoximesintramolecular cycloadditionnitrogen heterocycles |
| spellingShingle | Irina A. Mironova Valentine G. Nenajdenko Pavel S. Postnikov Akio Saito Mekhman S. Yusubov Akira Yoshimura Efficient Catalytic Synthesis of Condensed Isoxazole Derivatives via Intramolecular Oxidative Cycloaddition of Aldoximes Molecules hypervalent iodine hydroxy(aryl)iodonium catalysis aldoximes intramolecular cycloaddition nitrogen heterocycles |
| title | Efficient Catalytic Synthesis of Condensed Isoxazole Derivatives via Intramolecular Oxidative Cycloaddition of Aldoximes |
| title_full | Efficient Catalytic Synthesis of Condensed Isoxazole Derivatives via Intramolecular Oxidative Cycloaddition of Aldoximes |
| title_fullStr | Efficient Catalytic Synthesis of Condensed Isoxazole Derivatives via Intramolecular Oxidative Cycloaddition of Aldoximes |
| title_full_unstemmed | Efficient Catalytic Synthesis of Condensed Isoxazole Derivatives via Intramolecular Oxidative Cycloaddition of Aldoximes |
| title_short | Efficient Catalytic Synthesis of Condensed Isoxazole Derivatives via Intramolecular Oxidative Cycloaddition of Aldoximes |
| title_sort | efficient catalytic synthesis of condensed isoxazole derivatives via intramolecular oxidative cycloaddition of aldoximes |
| topic | hypervalent iodine hydroxy(aryl)iodonium catalysis aldoximes intramolecular cycloaddition nitrogen heterocycles |
| url | https://www.mdpi.com/1420-3049/27/12/3860 |
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