Next Article in Journal
Anti-Metastatic Properties of a Marine Bacterial Exopolysaccharide-Based Derivative Designed to Mimic Glycosaminoglycans
Next Article in Special Issue
Clean Transformation of Ethanol to Useful Chemicals. The Behavior of a Gold-Modified Silicalite Catalyst
Previous Article in Journal
Chemoinformatics in the New Era: From Molecular Dynamics to Systems Dynamics
Previous Article in Special Issue
Au-Based Catalysts: Electrochemical Characterization for Structural Insights
Article Menu
Issue 3 (March) cover image

Export Article

Open AccessArticle
Molecules 2016, 21(3), 307; doi:10.3390/molecules21030307

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

1
Laboratory of Heterocyclic Chemistry Natural Products and Reactivity/LCHPNR, Department of Chemistry, Faculty of Science, University of Monastir, 5000 Monastir, Tunisia
2
Institut UTINAM—UMR CNRS 6213, Université de Franche-Comté, 16 Route de Gray, 25030 Besançon, France
3
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)
View Full-Text   |   Download PDF [2330 KB, uploaded 4 March 2016]   |  

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. 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
Figures

Figure 1

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

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.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top