title: Synthesis of Isoxazole and 1,2,3-Triazole Isoindole Derivatives via Silver- and Copper-Catalyzed 1,3-Dipolar Cycloaddition Reaction.
abstract: The CuI- or Ag₂CO₃-catalyzed [3+2] cycloaddition of propargyl-substituted dihydroisoindolin-1-one (3) with arylnitrile oxides 1a-d (Ar = Ph, p-MeC₆H₄, p-MeOC₆H₄, p-ClC₆H₄) produces in good yields novel 3,5-disubstituted isoxazoles 4 of the ethyl-2-benzyl-3-oxo-1-((3-arylisoxazol-5yl)methyl)-2,3-dihydro-1H-isoindole-1-carboxylate type. With aryl azides 2a-d (Ar = Ph, p-MeC₆H₄, p-OMeC₆H₄, p-ClC₆H₄), a series of 1,4-disubstituted 1,2,3-triazoles 6 (ethyl-2-benzyl-3-oxo-1-((1-aryl-1H-1,2,3-triazol-4-yl)methyl)-2,3-dihydro-1H-isoindole-1-carboxylates) was obtained. The reactions proceed in a regioselective manner affording exclusively racemic adducts 4 and 6. Compared to the uncatalyzed cycloaddition, the yields are significantly improved in the presence of CuI as catalyst, without alteration of the selectivity. The regio- and stereochemistry of the cycloadducts has been corroborated by an X-ray diffraction study of 4a, and in the case of 6a by XH-correlation and HMBC spectra.
authors.affiliation: Laboratory of Heterocyclic Chemistry Natural Products and Reactivity/LCHPNR, Department of Chemistry, Faculty of Science, University of Monastir, 5000 Monastir, Tunisia. mehdiram@yahoo.fr.
authors.forename: Mohamed Mehdi
authors.initials: MM
authors.lastname: Rammah
authors.affiliation: Laboratory of Heterocyclic Chemistry Natural Products and Reactivity/LCHPNR, Department of Chemistry, Faculty of Science, University of Monastir, 5000 Monastir, Tunisia. wafa.gati@yahoo.fr.
authors.forename: Wafa
authors.initials: W
authors.lastname: Gati
authors.affiliation: Laboratory of Heterocyclic Chemistry Natural Products and Reactivity/LCHPNR, Department of Chemistry, Faculty of Science, University of Monastir, 5000 Monastir, Tunisia. mtiraoui1hasan@gmail.com.
authors.forename: Hasan
authors.initials: H
authors.lastname: Mtiraoui
authors.affiliation: Laboratory of Heterocyclic Chemistry Natural Products and Reactivity/LCHPNR, Department of Chemistry, Faculty of Science, University of Monastir, 5000 Monastir, Tunisia. rammahmbaker@gmail.com.
authors.forename: Mohamed El Baker
authors.initials: Mel B
authors.lastname: Rammah
authors.affiliation: Institut UTINAM-UMR CNRS 6213, Université de Franche-Comté, 16 Route de Gray, 25030 Besançon, France. ciamalak@yahoo.fr.
authors.forename: Kabula
authors.initials: K
authors.lastname: Ciamala
authors.affiliation: Institut UTINAM-UMR CNRS 6213, Université de Franche-Comté, 16 Route de Gray, 25030 Besançon, France. michael.knorr@univ-fcomte.fr.
authors.forename: Michael
authors.initials: M
authors.lastname: Knorr
authors.affiliation: Institut de Chimie Moléculaire-UMR CNRS 6302, Université de Bourgogne, 21078 Dijon, France. Yoann.Rousselin@u-bourgogne.fr.
authors.forename: Yoann
authors.initials: Y
authors.lastname: Rousselin
authors.affiliation: Institut de Chimie Moléculaire-UMR CNRS 6302, Université de Bourgogne, 21078 Dijon, France. Marek.Kubicki@u-bourgogne.fr.
authors.forename: Marek M
authors.initials: MM
authors.lastname: Kubicki
mesh_terms: D002384:Catalysis; D003300:Copper; D018360:Crystallography, X-Ray; D061565:Cycloaddition Reaction; D054833:Isoindoles / Q000138:chemical synthesis* / Q000737:chemistry; D007555:Isoxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D012834:Silver; D013055:Spectrophotometry, Infrared; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D054833:Isoindoles; D007555:Isoxazoles; D014230:Triazoles; D012834:Silver; D003300:Copper
keywords: 1,2,3-triazoles; [3+2] dipolar cycloaddition; arylazides; arylnitrile oxides; isoxazole