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二氧化硅包覆磁铁矿纳米粒子负载的铜(II)-美沙拉嗪配合物的设计、制备及其在绿色多组分合成高取代4-色烯和吡啶中的催化性能研究

Design and Preparation of Copper(II)-Mesalamine Complex Functionalized on Silica-Coated Magnetite Nanoparticles and Study of Its Catalytic Properties for Green and Multicomponent Synthesis of Highly Substituted 4-Chromenes and Pyridines.

作者信息

Taherkhani Hooman, Ramazani Ali, Sajjadifar Sami, Aghahossieini Hamideh, Rezaei Aram

机构信息

Department of Chemistry, Faculty of Science, University of Zanjan, Zanjan 45371-38791, Iran.

Department of Biotechnology, Research Institute of Modern Biological Techniques (RIMBT), University of Zanjan, Zanjan 45371-38791, Iran.

出版信息

ACS Omega. 2022 Apr 19;7(17):14972-14984. doi: 10.1021/acsomega.2c00731. eCollection 2022 May 3.

Abstract

In the present study, a green and ecofriendly nanocatalyst was synthesized through functionalization of 2,4,6-trichloro-1,3,5-triazine (TCT) and mesalamine on silica-coated magnetic nanoparticles (MNPs), then coordination with Cu without agglomeration, consecutively. The silica-coated MNPs functionalized with the Cu(*II)-mesalamine complex was (FeO@SiO@NH-TCT-mesalamine-Cu(II) MNPs) completely characterized by FT-IR, XRD, EDX, FESEM, TEM, VSM, TGA, and BET analyses. Afterward, the activity of the novel catalyst was investigated in the synthesis of chromene heterocycles, which were an important group of organic compounds. The activity of FeO@SiO@NH-TCT-mesalamine-Cu(II) MNPs as a high-performance heterogeneous nanocatalyst was evaluated for the synthesis of 2-amino-4-aryl-6-(phenylthio)pyridine-3,5-dicarbonitriles and 2-amino-4-chromenes via aromatic aldehydes, malononitrile, and enolizable C-H acids (resorcinol, 2-hydroxynaphthalene-1,4-dione, and benzenethiol) in ethanol under reflux conditions. FeO@SiO-TCT-mesalamine-Cu(II) could be quickly separated using an external magnet and reused nine times without a remarkable reduction of its catalytic activity.

摘要

在本研究中,通过将2,4,6-三氯-1,3,5-三嗪(TCT)和美沙拉嗪在二氧化硅包覆的磁性纳米颗粒(MNPs)上进行功能化,然后连续与铜配位且不发生团聚,合成了一种绿色环保的纳米催化剂。用傅里叶变换红外光谱(FT-IR)、X射线衍射(XRD)、能谱分析(EDX)、场发射扫描电子显微镜(FESEM)、透射电子显微镜(TEM)、振动样品磁强计(VSM)、热重分析(TGA)和比表面积分析(BET)对用铜(II)-美沙拉嗪配合物功能化的二氧化硅包覆的MNPs(FeO@SiO@NH-TCT-美沙拉嗪-Cu(II)MNPs)进行了全面表征。随后,研究了该新型催化剂在合成色烯杂环化合物中的活性,色烯杂环化合物是一类重要的有机化合物。评估了FeO@SiO@NH-TCT-美沙拉嗪-Cu(II)MNPs作为高性能多相纳米催化剂在乙醇回流条件下通过芳香醛、丙二腈和可烯醇化的C-H酸(间苯二酚、2-羟基萘-1,4-二酮和苯硫酚)合成2-氨基-4-芳基-6-(苯硫基)吡啶-3,5-二甲腈和2-氨基-4-色烯的活性。FeO@SiO-TCT-美沙拉嗪-Cu(II)可以用外部磁铁快速分离,并重复使用九次,其催化活性没有明显降低。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/73a4/9089390/4cc25d952531/ao2c00731_0013.jpg

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