Magnetic Sulfonated Melamine-Formaldehyde Resin as an Efficient Catalyst for the Synthesis of Antioxidant and Antimicrobial Pyrazolone Derivatives

Abstract

Sulfonated polymer-based materials, among heterogeneous catalysts, are frequently utilized in chemical transformations due to their outstanding chemical and physical durability. In this regard, a magnetic sulfonated melamine–formaldehyde resin (MSMF) catalyst was successfully prepared from a mixture of sulfonated melamine–formaldehyde and Fe3O4 nanoparticles in two steps. MSMF was used as a heterogeneous catalyst for the one-pot, three-component condensation of benzyl pyrazolyl naphthoquinones in water as a green solvent and 4-[(indol-3-yl)-arylmethyl]-1-phenyl-3-methyl-5-pyrazolones. The antimicrobial and antioxidant activities of catalyst, benzyl pyrazolyl naphthoquinones, and 4-[(indol-3-yl)-arylmethyl]-1-phenyl-3-methyl-5-pyrazolones were evaluated using agar disk-diffusion and DPPH assays, respectively. The antioxidant activity of the catalyst and 4-[(indol-3-yl)-arylmethyl]-1-phenyl-3-methyl-5-pyrazolones was found to be 75% and 90%, respectively. Furthermore, catalyst, benzyl pyrazolyl naphthoquinones, and 4-[(indol-3-yl)-arylmethyl]-1-phenyl-3-methyl-5-pyrazolones exhibited antimicrobial activity against Staphylococcus aureus and Escherichia coli. In conclusion, MSMF is a superior catalyst for green chemical processes, owing to its high catalytic activity, stability, and reusability.

Magnetic poly(1,8-diaminonaphthalene)-nickel nanocatalyst for the synthesis of antioxidant and antibacterial isoxazole-5(4H)-ones derivatives

“…The reaction flask was filled with a combination of acetic acid (0.5 mL), phenylhydrazine (0.05 mol, 5 mL), and ethyl acetoacetate (0.05 mol, 6.2 mL), and heated to 90 °C for 60 min while being stirred. EtOH was used for crystallization once the liquid had cooled to 25 °C and 10–20 mL ether had been added to the mixture and filtered to remove the precipitate [ 37 ] .…”

Poly(aniline-co-melamine)@MnFe2O4 nanocatalyst for the synthesis of 4,4′-(arylmethylene) bis (1H-pyrazole-5-ol) derivatives, and 1,4- dihydropyrano[2,3-c]pyrazoles and evaluation of their antioxidant, and anticancer activities

“…For the synthesis of 3-methyl-1-phenyl-1H-pyrazole-5-ol, phenylhydrazine (0.05 mol, 5 ml), acetic acid (0.5 ml), and ethyl acetoacetate (0.05 mol, 6.2 ml) were stirred in the reaction vessel at 90°C for 1 hour. After cooling at room temperature, 10–20 ml ether was added to the mixture the precipitate was filtered, and the product was crystallized using ethanol ( Nezhad et al, 2022 ).…”

Synthesis of Nitrogen- and Oxygen-Containing Heterocycles Catalysed by Metal Nanoparticles Reported in 2022

“…Nezhad et al synthesised the magnetic sulfonated melamine-formaldehyde resin (MSMF) as reusable catalysts (five runs) to synthesise antioxidant and antimicrobial pyrazolone derivatives ( 93 ) from 2-hydroxy naphthoquinone ( 91 ), aldehyde ( 88 ) and 3-methyl-1-phenyl-1 H -pyrazol-5-ol ( 92 ; Scheme 25 ). 78 The catalysts were prepared by the polymerisation of 2,4,6-triamino triazine or melamine using formaldehyde and sodium bisulfite followed by acidification and functionalisation using Fe 3 O 4 MNPs. The structural integrities of these catalysts were characterised using elemental analysis, FT-IR, VSM, XRD, TG/DTG, FE-SEM, TEM, EDX and IEC.…”