Synthesis and catalytic application of a curcumin-based bio-MOF in one-pot preparation of tetrahydroquinazolinone derivatives via Biginelli reaction

In this work, a new curcumin-based bidentate linker ligand, CurOAc, including two -COO- moieties at positions-4 in phenyl rings, was designed, synthesized, and characterized. Accordingly, its corresponding zinc-organic framework, Zn-CurOAc, as a bio-metal-organic framework (MOF) has been prepared and evaluated in the one-pot three-component Biginelli condensation reaction of substituted aromatic aldehydes, urea, and dimedone in ethanol. Zn-CurOAc shows an excellent catalytic performance for the synthesis of tetrahydroquinazolinone derivatives at room temperature with high turnover frequency (TOF) values (5.43-10.86 h(-1)). The chemical structure of Zn-CurOAc was characterized by fourier-transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), inductively coupled plasma optical emission spectrometry (ICP-OES), field emission-scanning electron microscopy (FE-SEM), transmission electron microscope (TEM), energy dispersive X-ray (EDX), differential thermal analysis (DTA), and thermogravimetric analysis (TGA) techniques. This new catalytic approach was proceeded by the excellent isolated yields, short reaction times, and easy workup.

Automated summary

A new curcumin-based bidentate linker ligand, CurOAc, and its corresponding zinc-organic framework, Zn-CurOAc, were designed, synthesized and characterized. Zn-CurOAc showed excellent catalytic performance in the one-pot three-component Biginelli condensation reaction.