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Bread waste in the form of CoFe2O4@TBW catalyst was used as a green biocatalyst to synthesize pyranopyrazole and tetraketone derivatives

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Abstract

Bread scraps with transition metal oxide spinels were utilized to synthesize core–shell magnetic nanocatalyst. The prepared heterogeneous catalyst was characterized using Fourier transform infrared spectroscopy (FTIR), X-ray diffraction (XRD), scanning electron microscopy (SEM), Brunauer–Emmett–Teller (BET), thermogravimetric analysis (TGA), and transmission electron microscopy (TEM). This magnetic nanocatalyst opens up a new avenue to introduce a very useful and efficient catalytic system for the one-pot synthesis of tetraketone derivatives via Knoevenagel-Micheal reaction of 1,3 cyclohexanedione and benzaldehyde in ethanol as a green solvent at 50 °C, and one-pot four-component reaction of benzaldehyde, dimedone, ethyl acetoacetate, and hydrazine hydrate via tandem Knoevenagel-Micheal reaction for the synthesis of dihydropyrano[2,3-c] pyrazole derivatives in ethanol. The pharmaceutical properties of dihydropyrano[2,3-c] pyrazole and tetraketones make them both essential compounds. Moreover, the recyclability of the new heterogeneous magnetic catalyst does not significantly deteriorate its catalytic activity, and it can be easily recovered by an external magnet and reused ten times without significant loss of activity, making it environmentally friendly and economically feasible to perform the desired transformations. NBO calculations were carried out at the level of B3LYP/6–311 +  + G (d, p) to obtain the atoms' natural charge data to justify the reaction's mechanism.

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Funding

We gratefully acknowledge the funding support received for this project from the Sharif University of Technology (SUT), Islamic Republic of Iran.

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Authors and Affiliations

  1. Laboratory of Organic Synthesis and Natural Products, Department of Chemistry, Sharif University of Technology, Azadi Street, PO Box 111559516, Tehran, Iran

    Firouz Matloubi Moghaddam, Sara Aghili & Maryam Daneshfar

  2. Department of Microbial Biotechnology, School of Biology, College of Science, University of Tehran, Enghelab Avenue, Tehran, 14155-6655, Iran

    Hamid Moghimi

  3. Department of Chemistry, Faculty of Science, K. N, Toosi University of Technology, P.O. Box 15875-4416, Tehran, Iran

    Zahra Daneshfar

Authors
  1. Firouz Matloubi Moghaddam
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  2. Sara Aghili
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Contributions

FMM contributed to project administration, supervision, conceptualization, validation, resources, and funding acquisition. SA contributed to methodology, formal analysis, funding acquisition, visualization, data curation, software, and writing—original draft. MD contributed to data curation, formal analysis, investigation, methodology, writing—original draft, validation, and conceptualization. HM contributed to methodology, formal analysis, and validation. ZD contributed to data curation, formal analysis, conceptualization, investigation, methodology, writing—original draft, visualization, and writing—review and editing.

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Correspondence to Firouz Matloubi Moghaddam.

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Moghaddam, F.M., Aghili, S., Daneshfar, M. et al. Bread waste in the form of CoFe2O4@TBW catalyst was used as a green biocatalyst to synthesize pyranopyrazole and tetraketone derivatives. Res Chem Intermed 49, 1507–1543 (2023). https://doi.org/10.1007/s11164-022-04934-z

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