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https://www.ias.ac.in/article/fulltext/jcsc/132/0086

Aza-aurone; nitrilimine; spiropyrazoline; pyrazole; amide; sulfonamide

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 obtainedcycloadducts 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.

MOHAMMED CHALKHA¹ MOHAMED BAKHOUCH^{1 2} MOHAMED AKHAZZANE^{1 3} MOHAMED BOURASS⁴ YOHANN NICOLAS⁴ GHALI AL HOUARI¹ MOHAMED EL YAZIDI¹

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
2. Department of Chemistry, Faculty of Sciences, Chouaı¨b Doukkali University, P.O. Box 20, 24000 El Jadida, Morocco
3. Universite´ Sidi Mohamed Ben Abdellah, Cite´ de l’innovation, Fes, Morocco
4. Institut des Sciences Mole´culaires, UMR-CNRS 5255, Universite´ of Bordeaux, 351 cours de la Libe´ration, 33405 Talence Cedex, France

Published

11 July 2020

Manuscript received

8 March 2020

Manuscript revised

30 April 2020

Accepted

5 May 2020