Design and Preparation of Copper(II)-Mesalamine Complex Functionalized on Silica-Coated Magnetite Nanoparticles and Study of Its Catalytic Properties for Green and Multicomponent Synthesis of Highly Substituted 4 H-Chromenes and Pyridines

Hooman Taherkhani; Ali Ramazani; Sami Sajjadifar; Hamideh Aghahossieini; Aram Rezaei

doi:10.1021/acsomega.2c00731

Design and Preparation of Copper(II)-Mesalamine Complex Functionalized on Silica-Coated Magnetite Nanoparticles and Study of Its Catalytic Properties for Green and Multicomponent Synthesis of Highly Substituted 4 H-Chromenes and Pyridines

ACS Omega. 2022 Apr 19;7(17):14972-14984. doi: 10.1021/acsomega.2c00731. eCollection 2022 May 3.

Authors

Hooman Taherkhani¹, Ali Ramazani^{1

2}, Sami Sajjadifar³, Hamideh Aghahossieini¹, Aram Rezaei⁴

Affiliations

¹ Department of Chemistry, Faculty of Science, University of Zanjan, Zanjan 45371-38791, Iran.
² Department of Biotechnology, Research Institute of Modern Biological Techniques (RIMBT), University of Zanjan, Zanjan 45371-38791, Iran.
³ Department of Chemistry, Payame Noor University, PO BOX Tehran 19395-4697, Iran.
⁴ Nano Drug Delivery Research Center, Health Technology Institute, Kermanshah University of Medical Sciences, Kermanshah 1673-67145, Iran.

Abstract

In the present study, a green and ecofriendly nanocatalyst was synthesized through functionalization of 2,4,6-trichloro-1,3,5-triazine (TCT) and mesalamine on silica-coated magnetic nanoparticles (MNPs), then coordination with Cu²⁺ without agglomeration, consecutively. The silica-coated MNPs functionalized with the Cu(*II)-mesalamine complex was (Fe₃O₄@SiO₂@NH₂-TCT-mesalamine-Cu(II) MNPs) completely characterized by FT-IR, XRD, EDX, FESEM, TEM, VSM, TGA, and BET analyses. Afterward, the activity of the novel catalyst was investigated in the synthesis of chromene heterocycles, which were an important group of organic compounds. The activity of Fe₃O₄@SiO₂@NH₂-TCT-mesalamine-Cu(II) MNPs as a high-performance heterogeneous nanocatalyst was evaluated for the synthesis of 2-amino-4-aryl-6-(phenylthio)pyridine-3,5-dicarbonitriles and 2-amino-4H-chromenes via aromatic aldehydes, malononitrile, and enolizable C-H acids (resorcinol, 2-hydroxynaphthalene-1,4-dione, and benzenethiol) in ethanol under reflux conditions. Fe₃O₄@SiO₂-TCT-mesalamine-Cu(II) could be quickly separated using an external magnet and reused nine times without a remarkable reduction of its catalytic activity.