Efficient synthesis of benzoacridines and indenoquinolines catalyzed by acidic magnetic dendrimer

Abstract

A novel solid acid catalyst with recoverability, named as Fe3O4@SiO2@TAD-G2-SO3H, was successfully synthesized by immobilizing sulfonic acid groups on triazine dendrimer-modified magnetic nanoparticles. This nanomaterial structure and composition were thoroughly characterized using various analytical techniques, including thermogravimetric analysis (TGA), elemental analysis, Fourier transform infrared spectroscopy (FT-IR), energy-dispersive X-ray spectroscopy (EDX), elemental mapping, acid–base titration, X-ray diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), and vibrating sample magnetometry (VSM). The acid-decorated magnetic dendrimer was served as a highly effective catalyst for the synthesis of tetrahydrobenzo[c]acridin-8(9H)-one and benzo[h]indeno[1,2-b]quinoline-8-one derivatives. The reaction proceeded smoothly under mild conditions through the one-pot condensation of aromatic aldehydes, 1-naphthylamine, and either dimedone or 1,3-indanedione, affording the desired products in high yields ranging from 90 to 96%. The catalyst was easily separated from the reaction mixture by employing a magnetic field, allowing for its recycling up to five times with slight loss in its activity (only 10%). Nearly, quantitative recovery of catalyst (up to 95%) could be obtained from each run. So, this catalyst facilitates the reaction progress and simplifies the purification process. Other remarkable features of this method are operational simplicity, excellent yields, mild condition, and a wide range of substrate applicability.