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新型磁性丙磺酸基笼型倍半硅氧烷基有机硅(氧化亚铁@PMO-ICS-PrSOH)作为高效可重复使用的纳米反应器,用于可持续合成咪唑并嘧啶衍生物。

Novel magnetic propylsulfonic acid-anchored isocyanurate-based periodic mesoporous organosilica (Iron oxide@PMO-ICS-PrSOH) as a highly efficient and reusable nanoreactor for the sustainable synthesis of imidazopyrimidine derivatives.

机构信息

Pharmaceutical and Heterocyclic Compounds Research Laboratory, Department of Chemistry, Iran University of Science and Technology, Tehran, 1684613114, Iran.

出版信息

Sci Rep. 2020 Jun 30;10(1):10646. doi: 10.1038/s41598-020-67592-4.

Abstract

In this study, preparation and characterization of a new magnetic propylsulfonic acid-anchored isocyanurate bridging periodic mesoporous organosilica (Iron oxide@PMO-ICS-PrSOH) is described. The iron oxide@PMO-ICS-PrSOH nanomaterials were characterized by Fourier transform infrared spectroscopy, energy-dispersive X-ray spectroscopy and field emission scanning electron microscopy as well as thermogravimetric analysis, N adsorption-desorption isotherms and vibrating sample magnetometer techniques. Indeed, the new obtained materials are the first example of the magnetic thermally stable isocyanurate-based mesoporous organosilica solid acid. Furthermore, the catalytic activity of the Iron oxide@PMO-ICS-PrSOH nanomaterials, as a novel and highly efficient recoverable nanoreactor, was investigated for the sustainable heteroannulation synthesis of imidazopyrimidine derivatives through the Traube-Schwarz multicomponent reaction of 2-aminobenzoimidazole, C‒H acids and diverse aromatic aldehydes. The advantages of this green protocol are low catalyst loading, high to quantitative yields, short reaction times and the catalyst recyclability for at least four consecutive runs.

摘要

本研究描述了一种新型磁性丙磺酸基异氰脲酸酯桥联介孔有机硅(氧化铁@PMO-ICS-PrSOH)的制备和表征。通过傅里叶变换红外光谱、能谱和场发射扫描电子显微镜以及热重分析、N2 吸附-脱附等温线和振动样品磁强计技术对氧化铁@PMO-ICS-PrSOH 纳米材料进行了表征。实际上,新获得的材料是第一种基于磁性热稳定异氰脲酸酯的介孔有机硅固体酸。此外,作为一种新型高效可回收纳米反应器,氧化铁@PMO-ICS-PrSOH 纳米材料的催化活性通过 Traube-Schwarz 多组分反应,对 2-氨基苯并咪唑、C-H 酸和各种芳香醛的咪唑并嘧啶衍生物的可持续杂环合成进行了研究。该绿色方案的优点是催化剂负载量低、产率高(定量至 99%)、反应时间短,催化剂在至少四个连续运行中可回收利用。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4efd/7327082/355f97711093/41598_2020_67592_Fig1_HTML.jpg

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