N-(2-pyridylmethyl)-L-histidine 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 three-component Mannich-type reaction of ketones, aromatic aldehydes and anilines, to synthesize β-amino ketones in good to high yields. Mannich adducts were obtained in moderate to high diastereoselectivity, favoring anti isomer. The imidazole moiety of PMHis residue on catalyst plays an important role in the diastereoselectivity. PMHis@Fe3O4 MNPs were prepared via 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 analysis.