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一种使用磁性乙二胺四乙酸包覆的铜基纳米复合材料绿色合成生物活性2,3-二氢喹唑啉-4(1)-酮的有效方法。

An efficient approach for the green synthesis of biologically active 2,3-dihydroquinazolin-4(1)-ones using a magnetic EDTA coated copper based nanocomposite.

作者信息

Kohli Sahil, Rathee Garima, Hooda Sunita, Chandra Ramesh

机构信息

Drug Discovery & Development Laboratory, Department of Chemistry, University of Delhi Delhi-110007 India

Department of Chemistry, Acharya Narendra Dev College, University of Delhi Delhi-110019 India

出版信息

RSC Adv. 2023 Jan 11;13(3):1923-1932. doi: 10.1039/d2ra07496f. eCollection 2023 Jan 6.

Abstract

2,3-Dihydroquinazolinone derivatives are known for antiviral, antimicrobial, analgesic, anti-inflammatory, and anticancer activities. However, recent approaches used for their synthesis suffer from various drawbacks. Therefore, we have fabricated a highly efficient magnetic EDTA-coated catalyst, FeO@EDTA/CuI a simple approach. The ethylenediamine tetraacetic acid (EDTA) plays a crucial role by strongly trapping the catalytic sites of CuI nanoparticles on the surface of the FeO core. The designed nanocatalyst demonstrates its potential for the catalytic synthesis of 2,3-dihydroquinazolinones using 2-aminobenzamide with aldehydes as the reaction partners. The nanocatalyst was thoroughly characterized through X-ray diffraction (XRD), Fourier-transform infrared spectroscopy (FTIR), vibrating sample magnetometry (VSM), transmission electron microscopy (TEM), scanning electron microscopy (SEM), energy dispersive X-ray analysis (EDX), X-ray photoelectron spectroscopy (XPS) and inductively coupled plasma analysis (ICP). The physiochemically characterized nanocatalyst was tested for synthesis of 2,3-dihydroquinazolinones and higher yields of derivatives were obtained with less time duration. Moreover, the catalytic synthesis is easy to operate without the use of any kind of additives/bases. Furthermore, the catalyst was magnetically recoverable after the completion of the reaction and displayed reusability for six successive rounds without any loss in its catalytic efficiency (confirmed by XRD, SEM, and TEM of the recycled material) along with very low leaching of copper (2.12 ppm) and iron (0.06 ppm) ions. Also, the green metrics were found in correlation with the ideal values (such as factor (0.10), process mass intensity (1.10), carbon efficiency (96%) and reaction mass efficiency (90.62%)).

摘要

2,3-二氢喹唑啉酮衍生物以其抗病毒、抗菌、止痛、抗炎和抗癌活性而闻名。然而,最近用于其合成的方法存在各种缺点。因此,我们采用一种简单的方法制备了一种高效的磁性乙二胺四乙酸(EDTA)包覆催化剂FeO@EDTA/CuI。乙二胺四乙酸(EDTA)通过强烈捕获FeO核表面上CuI纳米颗粒的催化位点发挥关键作用。所设计的纳米催化剂展示了其利用2-氨基苯甲酰胺与醛作为反应伙伴催化合成2,3-二氢喹唑啉酮的潜力。通过X射线衍射(XRD)、傅里叶变换红外光谱(FTIR)、振动样品磁强计(VSM)、透射电子显微镜(TEM)、扫描电子显微镜(SEM)、能量色散X射线分析(EDX)、X射线光电子能谱(XPS)和电感耦合等离子体分析(ICP)对该纳米催化剂进行了全面表征。对经过物理化学表征的纳米催化剂进行了2,3-二氢喹唑啉酮合成测试,在更短的时间内获得了更高产率的衍生物。此外,催化合成操作简便,无需使用任何添加剂/碱。此外,反应完成后催化剂可通过磁性回收,并连续六轮显示出可重复使用性,其催化效率没有任何损失(通过回收材料的XRD、SEM和TEM证实),同时铜(2.12 ppm)和铁(0.06 ppm)离子的浸出率非常低。此外,还发现绿色指标与理想值相关(如E因子(0.10)、过程质量强度(1.10)、碳效率(96%)和反应质量效率(90.62%))。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fe5e/9832363/1e31a1b75051/d2ra07496f-f1.jpg

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