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. 2023 Sep 21;13(40):28030-28041.
doi: 10.1039/d3ra05289c. eCollection 2023 Sep 18.

BiCl3-catalyzed green synthesis of 4-hydroxy-2-quinolone analogues under microwave irradiation

Yousra Ouafa Bouone  1   2 , Abdeslem Bouzina  1 , Rayene Sayad  1 , Abdelhak Djemel  3 , Farouk Benaceur  3 , Abdelhalim Zoukel  4 , Malika Ibrahim-Ouali  5 , Nour-Eddine Aouf  1 , Fouzia Bouchareb  2   6
Affiliations

BiCl3-catalyzed green synthesis of 4-hydroxy-2-quinolone analogues under microwave irradiation

Yousra Ouafa Bouone et al. RSC Adv. .

Abstract

Traditional chemical synthesis, which involves the use of dangerous protocols, hazardous solvents, and toxic products and catalysts, is considered environmentally inappropriate and harmful to human health. Bearing in mind its numerous drawbacks, it has become crucial to substitute conventional chemistry with green chemistry which is safer, more ecofriendly and more effective in terms of time and selectivity. Elaborating synthetic protocols producing interesting new compounds using both microwave heating and heterogeneous non-toxic catalysts is acknowledged as a green approach that avoids many classical chemistry-related problems. In the current study, β-enaminones were used as precursors to the synthesis of modified 4-hydroxy-2-quinolone analogues. The synthesis was monitored in a benign way under microwave irradiation and was catalyzed by bismuth chloride III in an amount of 20 mol%. This method is privileged by using a non-corrosive, non-toxic, low-cost and available bismuth Lewis acid catalyst that has made it more respectful to the demands of green chemistry. The synthesized compounds were obtained in moderate to good yields (51-71%) and were characterized by 1H, 13C NMR, and IR spectroscopy as well as elemental analysis. Compound 5i was subjected to a complete structural elucidation using the X-ray diffraction method, and the results show the obtention of the enolic tautomeric form.

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Conflict of interest statement

The authors declare that they have no competing interests.

Figures

Scheme 1
Scheme 1. Main tautomeric forms of 4-hydroxyquinolin-2-one.
Scheme 2
Scheme 2. Synthetic green route leading to 4-hydroxyquinolin-2-one analogues.
Scheme 3
Scheme 3. Model reaction for the synthesis of 4-hydroxy-2-quinolone analogue.
Fig. 1
Fig. 1. Obtained tautomeric forms for compound 5m.
Scheme 4
Scheme 4. Mechanistic proposal for the BiCl3-catalyzed synthesis of 4-hydroxy-2-quinolone analogues.
Fig. 2
Fig. 2. ORTEP diagram of compound 5i.
Fig. 3
Fig. 3. Crystal packing diagram of compound 5i viewed along the a-axis (H-bonds and short contacts are represented as blue dashed sticks).
See this image and copyright information in PMC

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