Direct ring fluorination of 3-substituted 5-(1,3-dioxane) acetal isoxazoles: application to the formal synthesis of a bioactive fluorinated isoxazole
The access to a novel variety of 4-fluorinated isoxazoles bearing an aryl or alkyl group at the C-3 position and an acetal fragment at the C-5 position has been achieved through a direct fluorination using N-fluorobenzenesulfonimide (NFSI) with yields up to 75%. This method was transposed to gram-sc...
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Académie des sciences
2024-02-01
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| Series: | Comptes Rendus. Chimie |
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| Online Access: | https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.278/ |
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| author | Bacheley, Lucas Guillamot, Gérard Phansavath, Phannarath Ratovelomanana-Vidal, Virginie |
| author_facet | Bacheley, Lucas Guillamot, Gérard Phansavath, Phannarath Ratovelomanana-Vidal, Virginie |
| author_sort | Bacheley, Lucas |
| collection | DOAJ |
| description | The access to a novel variety of 4-fluorinated isoxazoles bearing an aryl or alkyl group at the C-3 position and an acetal fragment at the C-5 position has been achieved through a direct fluorination using N-fluorobenzenesulfonimide (NFSI) with yields up to 75%. This method was transposed to gram-scale and has been applied to the formal synthesis of a bioactive compound that increases CFTR (Cystic Fibrosis Transmembrane Conductance Regulator) activity. |
| format | Article |
| id | doaj-art-10f7ad589cea47c99493358e557707d2 |
| institution | Kabale University |
| issn | 1878-1543 |
| language | English |
| publishDate | 2024-02-01 |
| publisher | Académie des sciences |
| record_format | Article |
| series | Comptes Rendus. Chimie |
| spelling | doaj-art-10f7ad589cea47c99493358e557707d22025-02-07T13:40:29ZengAcadémie des sciencesComptes Rendus. Chimie1878-15432024-02-0127S2333810.5802/crchim.27810.5802/crchim.278Direct ring fluorination of 3-substituted 5-(1,3-dioxane) acetal isoxazoles: application to the formal synthesis of a bioactive fluorinated isoxazoleBacheley, Lucas0Guillamot, Gérard1Phansavath, Phannarath2Ratovelomanana-Vidal, Virginie3https://orcid.org/0000-0003-1167-1195PSL University, Chimie ParisTech, CNRS UMR 8060, Institute of Chemistry for Life and Health Sciences, CSB2D Team, 75005 Paris, France; SEQENS, 2-8 rue de Rouen, ZI de Limay-Porcheville, 78440 Porcheville, FranceSEQENS, 2-8 rue de Rouen, ZI de Limay-Porcheville, 78440 Porcheville, FrancePSL University, Chimie ParisTech, CNRS UMR 8060, Institute of Chemistry for Life and Health Sciences, CSB2D Team, 75005 Paris, FrancePSL University, Chimie ParisTech, CNRS UMR 8060, Institute of Chemistry for Life and Health Sciences, CSB2D Team, 75005 Paris, FranceThe access to a novel variety of 4-fluorinated isoxazoles bearing an aryl or alkyl group at the C-3 position and an acetal fragment at the C-5 position has been achieved through a direct fluorination using N-fluorobenzenesulfonimide (NFSI) with yields up to 75%. This method was transposed to gram-scale and has been applied to the formal synthesis of a bioactive compound that increases CFTR (Cystic Fibrosis Transmembrane Conductance Regulator) activity.https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.278/FluorinationIsoxazolesHeterocycles |
| spellingShingle | Bacheley, Lucas Guillamot, Gérard Phansavath, Phannarath Ratovelomanana-Vidal, Virginie Direct ring fluorination of 3-substituted 5-(1,3-dioxane) acetal isoxazoles: application to the formal synthesis of a bioactive fluorinated isoxazole Comptes Rendus. Chimie Fluorination Isoxazoles Heterocycles |
| title | Direct ring fluorination of 3-substituted 5-(1,3-dioxane) acetal isoxazoles: application to the formal synthesis of a bioactive fluorinated isoxazole |
| title_full | Direct ring fluorination of 3-substituted 5-(1,3-dioxane) acetal isoxazoles: application to the formal synthesis of a bioactive fluorinated isoxazole |
| title_fullStr | Direct ring fluorination of 3-substituted 5-(1,3-dioxane) acetal isoxazoles: application to the formal synthesis of a bioactive fluorinated isoxazole |
| title_full_unstemmed | Direct ring fluorination of 3-substituted 5-(1,3-dioxane) acetal isoxazoles: application to the formal synthesis of a bioactive fluorinated isoxazole |
| title_short | Direct ring fluorination of 3-substituted 5-(1,3-dioxane) acetal isoxazoles: application to the formal synthesis of a bioactive fluorinated isoxazole |
| title_sort | direct ring fluorination of 3 substituted 5 1 3 dioxane acetal isoxazoles application to the formal synthesis of a bioactive fluorinated isoxazole |
| topic | Fluorination Isoxazoles Heterocycles |
| url | https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.278/ |
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