N-(2 Functionalized Fe3O4 Magnetic Nanoparticles as an Efficient Catalyst for Synthesis of β-Amino Ketones

Abstract

N-(2-pyridylmethyl)-L-histidine functionalized Fe3O4 magnetic nanoparticles (PMHis@Fe3O4 MNPs) efficiently catalyzed the three-component Mannish-type reaction of ketones, aromatic aldehydes, and anilines to synthesize beta-amino ketones in good to high yields. Mannich adducts were obtained in moderate to high diastereoselectivity, favoring anti isomers. The imidazole moiety of PMHis residue on a catalyst plays an important role in the diastereoselectivity. PMHis@Fe3O4 MNPs were prepared by the simple coprecipitation from an aqueous solution of Fe2+ and Fe3+ ions using NH4OH in the presence of L-histidine, followed by reductive amination with 2-pyridine carbaldehyde in the presence of NaBH4. Obtained PMHis@Fe3O4 MNPs were characterized by FT-IR, XRD, VSM, BET, TGA, SEM, EDX, and TEM analyses. (C) 2020 Sharif University of Technology. All rights reserved.