4.5 Article

Complexation of guanidino containing l-arginine with nickel on silica-modified Hercynite MNPs: a novel catalyst for the Hantzsch synthesis of polyhydroquinolines and 2,3-Dihydroquinazolin-4(1H)-ones

Journal

RESEARCH ON CHEMICAL INTERMEDIATES
Volume 48, Issue 6, Pages 2641-2663

Publisher

SPRINGER
DOI: 10.1007/s11164-022-04706-9

Keywords

Hercynite@SiO2-l-Arginine-Ni; Hantzsch reaction; Polyhydroquinoline; Cyclocondensation; 2; 3-dihydroquinazolin-4(1H)-one

Funding

  1. Ilam University, Ilam, Iran
  2. Bu-Ali Sina University, Hamedan, Iran

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In this study, a novel amino acid-based Ni complex was immobilized on SiO2-modified Hercynite magnetic nanoparticles to prepare a highly active catalytic system for various reactions. The heterogenized catalyst showed excellent thermal stability and could be easily separated and reused due to its magnetic and heterogeneous nature.
In this study, a novel amino acid-based Ni complex was immobilized on SiO2-modified Hercynite magnetic nanoparticles as the support to prepare the heterogenized guanidino-nickel catalyst (Hercynite@SiO2-l-Arginine-Ni). The uniform surface morphologies of these nanoparticles were characterized using SEM. Thermogravimetric analyses indicated that the [Hercynite@SiO2-l-Arginine-Ni] nanocomposite possessed reliable thermal stability. The homogeneous dispersion of nickel species on the surface of the amino acid-modified Hercynite was characterized using X-ray mapping and XRD. The catalysis studies showed that this heterogenized l-Arginine-Ni magnetic complex was highly active for the asymmetric Hantzsch synthesis of polyhydroquinolines and cyclocondensation of anthranilamide with aromatic aldehydes to generate 2,3-dihydroquinazolin-4(1H)-ones. In addition, the magnetic and heterogeneous nature of Hercynite core allows the easy separation of the catalyst by magnetic decantation. Besides, the [Hercynite@SiO2-l-Arginine-Ni] can be reused for at least 5 catalytic cycles for both of the mentioned reactions without an obvious drop in its activity.

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