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Molecules 2016, 21(3), 307;

Synthesis of Isoxazole and 1,2,3-Triazole Isoindole Derivatives via Silver- and Copper-Catalyzed 1,3-Dipolar Cycloaddition Reaction

Laboratory of Heterocyclic Chemistry Natural Products and Reactivity/LCHPNR, Department of Chemistry, Faculty of Science, University of Monastir, 5000 Monastir, Tunisia
Institut UTINAM—UMR CNRS 6213, Université de Franche-Comté, 16 Route de Gray, 25030 Besançon, France
Institut de Chimie Moléculaire—UMR CNRS 6302, Université de Bourgogne, 21078 Dijon, France
Dedicated to the memory of Professor Bernard Laude, deceased in 2015.
Authors to whom correspondence should be addressed.
Academic Editor: Sonia A. C. Carabineiro
Received: 16 January 2016 / Revised: 23 February 2016 / Accepted: 26 February 2016 / Published: 4 March 2016
(This article belongs to the Special Issue Coinage Metal (Copper, Silver, and Gold) Catalysis)
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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. View Full-Text
Keywords: [3+2] dipolar cycloaddition; arylnitrile oxides; arylazides; isoxazole; 1,2,3-triazoles [3+2] dipolar cycloaddition; arylnitrile oxides; arylazides; isoxazole; 1,2,3-triazoles

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Rammah, M.M.; Gati, W.; Mtiraoui, H.; Rammah, M.E.B.; Ciamala, K.; Knorr, M.; Rousselin, Y.; Kubicki, M.M. Synthesis of Isoxazole and 1,2,3-Triazole Isoindole Derivatives via Silver- and Copper-Catalyzed 1,3-Dipolar Cycloaddition Reaction. Molecules 2016, 21, 307.

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