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色氨酸功能化MCM-41负载锌配合物作为一种高效且有前景的可重复使用纳米催化剂,用于通过贝蒂反应一锅法合成氨基苄基喹诺醇和萘酚的三组分反应。

Zn Complex on Tryptophan-Functionalized MCM-41 as an Efficient and Promising Reusable Nanocatalyst in One-Pot Three-Component Synthesis of Amino Benzyl Quinolinols and Naphthols via a Betti Reaction.

作者信息

Hamedimehr Shakila, Ojaghi Aghbash Khadijeh, Noroozi Pesyan Nader

机构信息

Department of Organic Chemistry, Faculty of Chemistry, Urmia University, 57159Urmia, Iran.

出版信息

ACS Omega. 2023 Feb 21;8(9):8227-8236. doi: 10.1021/acsomega.2c05723. eCollection 2023 Mar 7.

Abstract

In this research, a Zn transition metallic complex on functionalized mesopore silica MCM-41 has been designed and utilized as an effective, recoverable, and thermally stable heterogeneous nanocatalyst in the formation of the C-C bond. Also, the synthesis of amino benzyl quinolinols and amino benzyl naphthol derivatives was performed by the three-component reaction of Betti from aromatic aldehydes, type II amines, and 8-hydroxyquinoline and 1-naphthol in the presence of the MCM-41-tryptophan-Zn nanocatalyst under reflux conditions. The short reaction times, high efficiency of the products, the easy separation of catalysts due to their heterogeneity, and their reusability are the advantages of this method. Finally, the nature of catalysts was studied by using some techniques such as the Fourier transform infrared spectrum, energy-dispersive spectroscopy, hot filtration test, transmission electron microscopy, scanning electron microscopy, X-ray diffraction, inductively coupled plasma optical emission spectrometry, and N adsorption-desorption (BET). The synthesized heterogeneous catalysts showed perfect catalytic activity and also good recyclability in the Betti reaction. They could be reused at least for five consecutive cycles without significant loss of their catalytic activities.

摘要

在本研究中,已设计并利用功能化介孔二氧化硅MCM - 41上的锌过渡金属配合物作为一种有效、可回收且热稳定的多相纳米催化剂用于C - C键的形成。此外,在MCM - 41 - 色氨酸 - 锌纳米催化剂存在下,于回流条件下通过芳香醛、II型胺与8 - 羟基喹啉以及1 - 萘酚的贝蒂三组分反应合成了氨基苄基喹啉醇和氨基苄基萘酚衍生物。反应时间短、产物效率高、由于催化剂的多相性易于分离以及可重复使用是该方法的优点。最后,通过傅里叶变换红外光谱、能量色散光谱、热过滤试验、透射电子显微镜、扫描电子显微镜、X射线衍射、电感耦合等离子体发射光谱以及N吸附 - 脱附(BET)等技术研究了催化剂的性质。合成的多相催化剂在贝蒂反应中表现出完美的催化活性以及良好的可回收性。它们可以至少连续重复使用五个循环而其催化活性无显著损失。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dc3b/9996610/bc120a569f00/ao2c05723_0003.jpg

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