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Design, synthesis and characterization of functionalized pyrazole derivatives bearing amide and sulfonamide moieties from aza-aurones

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Abstract

In this work, we report the synthesis of new pyrazole derivatives bearing amide and sulfonamide frameworks from aza-aurones. Firstly, the intermediate spiropyrazolines were obtained through a highly regioselective 1,3-dipolar cycloaddition of nitrilimines with aza-aurones. Subsequently, the obtained cycloadducts were subjected to hydrochloric acid in hot ethanol which conducts to 5-(2-aminobenzoyl)-3,4-diaryl-1-phenylpyrazoles. Finally, the target compounds were obtained separately by the action of acetic anhydride, benzoyl chloride and tosyl chloride on the intermediates 2-aminobenzoylpyrazoles, respectively. Structures of all the synthesized compounds were established using IR, 1H NMR and 13C NMR and mass spectroscopy.

Graphic Abstract

Synthesis and characterization of novel heterocyclic systems encompassing pyrazole derivatives from aza-aurones are reported. The synthetic routes used in this work are efficient and relevant, involving the 1,3-dipolar cycloaddition and alkylation reactions. The outcomes show that spectroscopic data fit the structure of all synthesized compounds.

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Acknowledgements

The authors are grateful to “Cité de l’Innovation” of Sidi Mohamed Ben Abdellah University for spectroscopic measurement. This work has been supported by the CESAMO platform (Bordeaux University).

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Authors and Affiliations

  1. Engineering Laboratory of Organometallic and Molecular Materials and Environment, Faculty of Sciences Dhar EL Mahraz, University Sidi Mohamed Ben Abdellah, P.O. Box 1796 (Atlas), 30000, Fes, Morocco

    Mohammed Chalkha, Mohamed Bakhouch, Mohamed Akhazzane, Ghali Al Houari & Mohamed El Yazidi

  2. Department of Chemistry, Faculty of Sciences, Chouaïb Doukkali University, P.O. Box 20, 24000, El Jadida, Morocco

    Mohamed Bakhouch

  3. Université Sidi Mohamed Ben Abdellah, Cité de l’innovation, Fes, Morocco

    Mohamed Akhazzane

  4. Institut des Sciences Moléculaires, UMR-CNRS 5255, Université of Bordeaux, 351 cours de la Libération, 33405, Talence Cedex, France

    Mohamed Bourass & Yohann Nicolas

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  1. Mohammed Chalkha
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  2. Mohamed Bakhouch
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  3. Mohamed Akhazzane
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Correspondence to Mohamed El Yazidi.

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Chalkha, M., Bakhouch, M., Akhazzane, M. et al. Design, synthesis and characterization of functionalized pyrazole derivatives bearing amide and sulfonamide moieties from aza-aurones. J Chem Sci 132, 86 (2020). https://doi.org/10.1007/s12039-020-01792-3

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  • DOI: https://doi.org/10.1007/s12039-020-01792-3

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