Ferrocene‐tagged ionic liquid stabilized on silica‐coated magnetic nanoparticles: Efficient catalyst for the synthesis of 2‐amino‐3‐cyano‐4H‐pyran derivatives under solvent‐free conditions

• Published in: Applied organometallic chemistry 2018-01, Vol.32 (1), p.n/a
• Main Authors: Teimuri‐Mofrad, Reza, Gholamhosseini‐Nazari, Mahdi, Payami, Elmira, Esmati, Somayeh
• Format: Article
• Language: English
• Subjects: 2‐amino‐3‐cyano‐4H‐pyran; Aldehydes; Catalysis; Catalysts; Catalytic activity; Chemical synthesis; Chemistry; Derivatives; Energy transmission; ferrocene; Field emission microscopy; Fourier transforms; Ionic liquids; Ions; Iron oxides; magnetic nanocatalyst; Malononitrile; Naphthol; NMR; Nuclear magnetic resonance; Silicon dioxide; Solvents; solvent‐free
• ISSN: 0268-2605; 1099-0739
• DOI: 10.1002/aoc.3955

An advanced novel magnetic ionic liquid based on imidazolium tagged with ferrocene, a supported ionic liquid, is introduced as a recyclable heterogeneous catalyst. Catalytic activity of the novel nanocatalyst was investigated in one‐pot three‐component reactions of various aldehydes, malononitrile and 2‐naphthol for the facile synthesis of 2‐amino‐3‐cyano‐4H‐pyran derivatives under solvent‐free conditions without additional co‐catalyst or additive in air. For this purpose, we firstly synthesized and investigated 1‐(4‐ferrocenylbutyl)‐3‐methylimidazolium acetate, [FcBuMeIm][OAc], as a novel basic ferrocene‐tagged ionic liquid. This ferrocene‐tagged ionic liquid was then linked to silica‐coated nano‐Fe3O4 to afford a novel heterogeneous magnetic nanocatalyst, namely [Fe3O4@SiO2@Im‐Fc][OAc]. The synthesized novel catalyst was characterized using 1H NMR, 13C NMR, Fourier transform infrared and energy‐dispersive X‐ray spectroscopies, X‐ray diffraction, and transmission and field emission scanning electron microscopies. Combination of some unique characteristics of ferrocene and the supported ionic liquid developed the catalytic activity in a simple, efficient, green and eco‐friendly protocol. The catalyst could be reused several times without loss of activity. An advanced novel magnetic ionic liquid based on imidazolium tagged with ferrocene was designed and synthesized as a recyclable heterogeneous catalyst. The activity of the nanocatalyst was investigated for the facile synthesis of 2‐amino‐3‐cyano‐4H‐pyran derivatives under solvent‐free conditions.