Nitrile Oxide, Alkenes, Dipolar Cycloaddition, Isomerization and Metathesis Involved in the Syntheses of 2-Isoxazolines
The involvement of 1,3-dipolar cycloaddition (1,3-DP), double bond migration, metathesis, and nitrile oxide (including in situ-generated nitrile oxide) as dipoles, together with the C=C bond containing dipolarophiles, in the syntheses of 2-isoxazolines is presented. Methods for synthesizing isoxazol...
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MDPI AG
2023-03-01
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| Online Access: | https://www.mdpi.com/1420-3049/28/6/2547 |
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| author | Stanisław Krompiec Piotr Lodowski Aneta Kurpanik-Wójcik Bogumiła Gołek Angelika Mieszczanin Aleksandra Fijołek Marek Matussek Klaudia Kaszuba |
| author_facet | Stanisław Krompiec Piotr Lodowski Aneta Kurpanik-Wójcik Bogumiła Gołek Angelika Mieszczanin Aleksandra Fijołek Marek Matussek Klaudia Kaszuba |
| author_sort | Stanisław Krompiec |
| collection | DOAJ |
| description | The involvement of 1,3-dipolar cycloaddition (1,3-DP), double bond migration, metathesis, and nitrile oxide (including in situ-generated nitrile oxide) as dipoles, together with the C=C bond containing dipolarophiles, in the syntheses of 2-isoxazolines is presented. Methods for synthesizing isoxazolines (other than 1,3-DP cycloaddition) were also presented briefly. Various methods of nitrile oxide preparation, especially in situ-generated procedures, are presented. Special attention was paid to the application of various combinations of 1,3-DP cycloaddition with double bond migration (DBM) and with alkene metathesis (AM) in the syntheses of trisubstituted isoxazolines. Allyl compounds of the type QCH<sub>2</sub>CH=CH<sub>2</sub> (Q = ArO, ArS, Ar, and others) play the role of dipolarophile precursors in the combinations of DPC mentioned, DBM and AM. Mechanistic aspects of cycloadditions, i.e., concerted or stepwise reaction mechanism and their regio- and stereoselectivity are also discussed from experimental and theoretical points of view. Side reactions accompanying cycloaddition, especially nitrile oxide dimerization, are considered. 2-Isoxazoline applications in organic synthesis and their biological activity, broad utility in medicine, agriculture, and other fields were also raised. Some remaining challenges in the field of 1,3-DP cycloaddition in the syntheses of isoxazolines are finally discussed. |
| first_indexed | 2024-03-11T06:07:28Z |
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| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T06:07:28Z |
| publishDate | 2023-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-882dca94f7464dcbb70162719309566c2023-11-17T12:51:52ZengMDPI AGMolecules1420-30492023-03-01286254710.3390/molecules28062547Nitrile Oxide, Alkenes, Dipolar Cycloaddition, Isomerization and Metathesis Involved in the Syntheses of 2-IsoxazolinesStanisław Krompiec0Piotr Lodowski1Aneta Kurpanik-Wójcik2Bogumiła Gołek3Angelika Mieszczanin4Aleksandra Fijołek5Marek Matussek6Klaudia Kaszuba7Institute of Chemistry, Faculty of Science and Technology, University of Silesia, Bankowa 14, 40-007 Katowice, PolandInstitute of Chemistry, Faculty of Science and Technology, University of Silesia, Bankowa 14, 40-007 Katowice, PolandInstitute of Chemistry, Faculty of Science and Technology, University of Silesia, Bankowa 14, 40-007 Katowice, PolandInstitute of Chemistry, Faculty of Science and Technology, University of Silesia, Bankowa 14, 40-007 Katowice, PolandDepartment of Chemical Organic Technology and Petrochemistry, Faculty of Chemistry, Silesian University of Technology, B. Krzywoustego 4., 44-100 Gliwice, PolandInstitute of Chemistry, Faculty of Science and Technology, University of Silesia, Bankowa 14, 40-007 Katowice, PolandInstitute of Chemistry, Faculty of Science and Technology, University of Silesia, Bankowa 14, 40-007 Katowice, PolandInstitute of Chemistry, Faculty of Science and Technology, University of Silesia, Bankowa 14, 40-007 Katowice, PolandThe involvement of 1,3-dipolar cycloaddition (1,3-DP), double bond migration, metathesis, and nitrile oxide (including in situ-generated nitrile oxide) as dipoles, together with the C=C bond containing dipolarophiles, in the syntheses of 2-isoxazolines is presented. Methods for synthesizing isoxazolines (other than 1,3-DP cycloaddition) were also presented briefly. Various methods of nitrile oxide preparation, especially in situ-generated procedures, are presented. Special attention was paid to the application of various combinations of 1,3-DP cycloaddition with double bond migration (DBM) and with alkene metathesis (AM) in the syntheses of trisubstituted isoxazolines. Allyl compounds of the type QCH<sub>2</sub>CH=CH<sub>2</sub> (Q = ArO, ArS, Ar, and others) play the role of dipolarophile precursors in the combinations of DPC mentioned, DBM and AM. Mechanistic aspects of cycloadditions, i.e., concerted or stepwise reaction mechanism and their regio- and stereoselectivity are also discussed from experimental and theoretical points of view. Side reactions accompanying cycloaddition, especially nitrile oxide dimerization, are considered. 2-Isoxazoline applications in organic synthesis and their biological activity, broad utility in medicine, agriculture, and other fields were also raised. Some remaining challenges in the field of 1,3-DP cycloaddition in the syntheses of isoxazolines are finally discussed.https://www.mdpi.com/1420-3049/28/6/25472-isoxazolinesnitrile oxide1,3-dipolar cycloadditionallyl compoundsreaction mechanismisoxazolines in pharmacy |
| spellingShingle | Stanisław Krompiec Piotr Lodowski Aneta Kurpanik-Wójcik Bogumiła Gołek Angelika Mieszczanin Aleksandra Fijołek Marek Matussek Klaudia Kaszuba Nitrile Oxide, Alkenes, Dipolar Cycloaddition, Isomerization and Metathesis Involved in the Syntheses of 2-Isoxazolines Molecules 2-isoxazolines nitrile oxide 1,3-dipolar cycloaddition allyl compounds reaction mechanism isoxazolines in pharmacy |
| title | Nitrile Oxide, Alkenes, Dipolar Cycloaddition, Isomerization and Metathesis Involved in the Syntheses of 2-Isoxazolines |
| title_full | Nitrile Oxide, Alkenes, Dipolar Cycloaddition, Isomerization and Metathesis Involved in the Syntheses of 2-Isoxazolines |
| title_fullStr | Nitrile Oxide, Alkenes, Dipolar Cycloaddition, Isomerization and Metathesis Involved in the Syntheses of 2-Isoxazolines |
| title_full_unstemmed | Nitrile Oxide, Alkenes, Dipolar Cycloaddition, Isomerization and Metathesis Involved in the Syntheses of 2-Isoxazolines |
| title_short | Nitrile Oxide, Alkenes, Dipolar Cycloaddition, Isomerization and Metathesis Involved in the Syntheses of 2-Isoxazolines |
| title_sort | nitrile oxide alkenes dipolar cycloaddition isomerization and metathesis involved in the syntheses of 2 isoxazolines |
| topic | 2-isoxazolines nitrile oxide 1,3-dipolar cycloaddition allyl compounds reaction mechanism isoxazolines in pharmacy |
| url | https://www.mdpi.com/1420-3049/28/6/2547 |
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