Recyclable mesalamine-functionalized magnetic nanoparticles (mesalamine/GPTMS@SiO@FeO) for tandem Knoevenagel-Michael cyclocondensation: grinding technique for the synthesis of biologically active 2-amino-4-benzo[]pyran derivatives

• Published in: RSC advances 2023-11, Vol.13 (48), p.33566-33587
• Main Authors: Partovi, Mahdiyeh, Rezayati, Sobhan, Ramazani, Ali, Ahmadi, Yavar, Taherkhani, Hooman
• Format: Article
• ISSN: 2046-2069
• DOI: 10.1039/d3ra06560j

In the present study, mesalamine-functionalized on magnetic nanoparticles (mesalamine/GPTMS@SiO 2 @Fe 3 O 4 ) is fabricated as an efficient and magnetically recoverable nanocatalyst. The as-prepared nanocatalyst was successfully synthesized in three steps using a convenient and low-cost method via modification of the surface of Fe 3 O 4 nanoparticles with silica and GPTMS, respectively, to afford GPTMS@SiO 2 @Fe 3 O 4 . Finally, treatment with mesalamine as a powerful antioxidant generates the final nanocatalyst. Then, its structure was characterized by FT-IR, SEM, TEM, EDX, XRD, BET, VSM, and TGA techniques. The average size was found to be approximately 38 nm using TEM analysis and the average crystallite size was found to be approximately 27.02 nm using XRD analysis. In particular, the synthesized nanocatalyst exhibited strong thermal stability up to 400 °C and high magnetization properties. The activity of the synthesized nanocatalyst was evaluated in the tandem Knoevenagel-Michael cyclocondensation of various aromatic aldehydes, dimedone and malononitrile under a dry grinding method at room temperature to provide biologically active 2-amino-4 H -benzo[ b ]pyran derivatives products in a short time with good yields. The presented procedure offers several advantages including gram-scale synthesis, good green chemistry metrics (GCM), easy fabrication of the catalyst, atom economy (AE), no use of column chromatography, and avoiding the generation of toxic materials. Furthermore, the nanocatalyst can be reused for 8 cycles with no loss of performance by using an external magnet. Mesalamine-functionalized on magnetic nanoparticles (mesalamine/GPTMS@SiO 2 @Fe 3 O 4 ) is synthesized and characterized as an efficient and magnetically recoverable nanocatalyst for the synthesis of biologically active 2-amino-4 H -benzo[ b ]pyran derivatives products via grinding method.