A new nano-Fe3O4-supported organocatalyst based on 3,4-dihydroxypyridine: an efficient heterogeneous nanocatalyst for one-pot synthesis of pyrazolo[3,4-b]pyridines and pyrano[2,3-d]pyrimidines

摘要

A simple and practical strategy for the synthesis of a novel nano-Fe3O4-supported organocatalyst system based on 3,4-dihydroxypyridine (Fe3O4/Py) has been developed. The prepared catalyst was characterized using Fourier transform infrared spectroscopy, transmission and scanning electron microscopies, X-ray diffraction, vibrating sample magnetometry and energy-dispersive X-ray analysis. Accordingly, the Fe3O4/Py nanoparticles show a superparamagnetic property with a saturation magnetization of 61 emu g(-1), indicating potential application in magnetic separation technology. Our experimental results reveal that the pyridine-functionalized Fe3O4 nanoparticles are an efficient base catalyst for the domino condensation of various aromatic aldehydes, Meldrum's acid and 5-methylpyrazol-3-amine under very mild reaction condition and in the presence of ethanol solvent. Moreover, the synthesized catalyst was used for one-pot, three-component condensation of aromatic aldehydes with barbituric acid and malononitrile to produce 7-amino-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-H-1-pyrano[2,3-d]pyrimidine-6-carbonitriles. All reactions are completed in short times and all products are obtained in good to excellent yields. Also, notably, the catalyst was reused five times without significant degradation in catalytic activity and performance. Copyright (C) 2016 John Wiley & Sons, Ltd.