Open AccessDesign 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 4H-Chromenes and Pyridines
Author(s) -
Hooman Taherkhani,
Ali Ramazani,
Sami Sajjadifar,
Hamideh Aghahossieini,
Aram Rezaei
Publication year - 2022
Publication title -
acs omega
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.779
H-Index - 40
ISSN - 2470-1343
DOI - 10.1021/acsomega.2c00731
Subject(s) - malononitrile , catalysis , nuclear chemistry , surface modification , chemistry , resorcinol , copper , nanoparticle , magnetic nanoparticles , materials science , organic chemistry , nanotechnology
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 Cu 2+ without agglomeration, consecutively. The silica-coated MNPs functionalized with the Cu(*II)-mesalamine complex was (Fe 3 O 4 @SiO 2 @NH 2 -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 Fe 3 O 4 @SiO 2 @NH 2 -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-4 H -chromenes via aromatic aldehydes, malononitrile, and enolizable C-H acids (resorcinol, 2-hydroxynaphthalene-1,4-dione, and benzenethiol) in ethanol under reflux conditions. Fe 3 O 4 @SiO 2 -TCT-mesalamine-Cu(II) could be quickly separated using an external magnet and reused nine times without a remarkable reduction of its catalytic activity.