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Solvent-Free Regioselective Synthesis of Novel Isoxazoline and Pyrazoline N-Substituted Saccharin Derivatives Under Microwave Irradiation

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Chemistry of Heterocyclic Compounds Aims and scope

Novel isoxazoline and pyrazoline derivatives of N-substituted saccharin were synthesized in good yields by 1,3-dipolar cycloaddition of N-crotonoyl- or N-cinnamoylsaccharin as dipolarophile to arylnitrile oxides or nitrile imines using p-HAP300 as catalyst under solventfree microwave conditions. In this process, the yields were significantly improved compared to classical conditions without alteration of the selectivity. The regioselectivity as well as the nonthermal specific microwave effect are discussed.

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Authors and Affiliations

  1. Laboratoire de Chimie des Plantes et de Synthèse Organique et Bioorganique, URAC23, Université Mohammed V, B. P. 1014, Rabat, Morocco

    Aziza Saber, Mohsine Driowya, Soukaina Alaoui, Hamid Marzag & Khalid Bougrin

  2. Institut de Chimie de Nice, ICN, UMR 7272, Université Nice-Sophia Antipolis, 28 avenue de Valrose, 06108, Nice Cedex 2, France

    Luc Demange & Rachid Benhida

  3. Université Paris Descartes, Sorbonne Paris Cité, UFR des Sciences Pharmaceutiques, 4 avenue de l’Observatoire, Paris, 75006, France

    Luc Demange

  4. Université Paris Descartes, Sorbonne Paris Cité, UFR Biomédicale des Saints Pères, 45 rue des Saints Pères, Paris, 75006, France

    Luc Demange

  5. Instituto de Investigaciones Químicas, CSIC-Universidad de Sevilla, Avda. Américo Vespucio, 49, Isla de La Cartuja, 41092, Sevilla, Spain

    Eleuterio Álvarez

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  1. Aziza Saber
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  2. Mohsine Driowya
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  3. Soukaina Alaoui
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  7. Rachid Benhida
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  8. Khalid Bougrin
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Correspondence to Khalid Bougrin.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(1), 31–40

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Saber, A., Driowya, M., Alaoui, S. et al. Solvent-Free Regioselective Synthesis of Novel Isoxazoline and Pyrazoline N-Substituted Saccharin Derivatives Under Microwave Irradiation. Chem Heterocycl Comp 52, 31–40 (2016). https://doi.org/10.1007/s10593-016-1828-4

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