Affiliation:
1. Laboratoire de Chimie Organique et Analytique, Faculte des Sciences et Techniques, Universite Sultan Moulay Slimane, BP 523, 23000 Beni-Mellal, Morocco
2. Laboratoire de Chimie Analytique et Moleculaire, Faculte Polydisciplinaire, Universite Cadi Ayyad, BP 4162, 46000 Safi, Morocco
Abstract
Objective:
To synthesize novel bispyrazole heterocyclic molecules may have important
biological activities and thus can serve as good candidates for pharmaceutical applications.
Methods:
The bispyrazole derivatives 3a-m were prepared by the condensation reaction of
substituted aromatic aldehydes with 1,3-diketo-N-phenylpyrazole by using Mg/Al-LDH as a
heterogeneous catalyst under THF solvent at the refluxing temperature.
Results:
This protocol describes the synthesis of bioactive compounds under mild reaction
conditions, with good yields, and easiness of the catalyst separation from the reaction mixture.
Furthermore, a mechanistic study has been performed by using DFT calculations to explain
the observed selectivity of the condensation reaction between aryl aldehyde and 1,3-
diketo-N-phenylpyrazole via Knoevenagel reaction. The local electrophilicity/ nucleophilicity
explains correctly the experimental finding.
Conclusion:
In summary, the pharmacologically interesting bis-pyrazole derivatives were
synthesized through Mg/Al-LDH as a solid base catalyst, in THF as a solvent. The synthesized
bioactive compounds containing the pyrazole ring may have important biological activities
and thus can serve as good candidates for pharmaceutical applications. Therefore, the
catalyst Mg/Al-LDH showed high catalytic activity. Besides, a series of bispyrazole molecules
were synthesized with a good yield and easy separation of the catalyst by simple filtration.
Moreover, DFT calculations and reactivity indexes were used to explain the selectivity of the
condensation reaction between aryl benzaldehyde and 1,3-diketo-N-phenylpyrazole via
Knoevenagel reaction, and the results were in good agreement with the experimental finding.
Publisher
Bentham Science Publishers Ltd.
Cited by
3 articles.
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