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纳米有序聚丙烯腈接枝壳聚糖作为一种强大的生物聚合物催化剂,用于高效合成高度取代的吡咯衍生物。

Nano ordered polyacrylonitrile-grafted chitosan as a robust biopolymeric catalyst for efficient synthesis of highly substituted pyrrole derivatives.

作者信息

Zohrehvand Mahsa, Nashibi Niloufar, Dekamin Mohammad G, Sarvary Afshin

机构信息

Pharmaceutical and Heterocyclic Compounds Research Laboratory, Department of Chemistry, Iran University of Science and Technology, Tehran, 16846-13114, Iran.

Department of Chemistry, Babol Noshirvani University of Technology, Babol, 4714873113, Iran.

出版信息

Sci Rep. 2025 Jul 1;15(1):22183. doi: 10.1038/s41598-025-05504-0.

Abstract

A novel heterogeneous nanocatalyst was developed using chitosan, as a natural polysaccharide derived from crustacean shells, and its in-situ grafting by polyacrylonitrile to afford nano ordered polyacrylonitrile-modified chitosan (CS-g-PAN). The obtained CS-g-PAN nanomaterial was thoroughly analyzed using several appropriate spectroscopic, microscopic or analytical techniques, including EDS and FTIR spectroscopy, EDS elemental mapping, FESEM imaging, XRD, TGA and DTA, and N adsorption-desorption isotherm. The catalytic activity of multifunctional CS-g-PAN nanomaterial, as an organocatalyst, was evaluated in the green synthesis of highly substituted pyrrole derivatives through multi-component reactions strategy from corresponding α-haloketones, β-dicarbonyl compounds, and primary amines. This method offers several advantages, including high efficiency, short reaction times, ease of catalyst separation and recovery as well as recyclability for at least five cycles without significant loss of its activity. The catalyst's eco-friendly nature, lack of toxic transition metals, and mild reaction conditions make it a promising sustainable alternative for the Hantzsch synthesis of different pyrrole derivatives.

摘要

利用壳聚糖(一种源自甲壳类动物外壳的天然多糖)开发了一种新型多相纳米催化剂,并通过聚丙烯腈对其进行原位接枝,得到纳米有序聚丙烯腈改性壳聚糖(CS-g-PAN)。使用几种合适的光谱、显微镜或分析技术对所得的CS-g-PAN纳米材料进行了全面分析,包括能谱(EDS)和傅里叶变换红外光谱(FTIR)、EDS元素映射、场发射扫描电子显微镜(FESEM)成像、X射线衍射(XRD)、热重分析(TGA)和差热分析(DTA)以及氮吸附-脱附等温线。作为一种有机催化剂,多功能CS-g-PAN纳米材料的催化活性通过多组分反应策略从相应α-卤代酮、β-二羰基化合物和伯胺绿色合成高取代吡咯衍生物进行了评估。该方法具有几个优点,包括高效率、短反应时间、易于催化剂分离和回收以及至少可循环使用五个周期且活性无显著损失。催化剂的环保性质、不含有毒过渡金属以及温和的反应条件使其成为汉茨希合成不同吡咯衍生物的一种有前景的可持续替代方法。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9af8/12214970/5cecb45ed39c/41598_2025_5504_Fig1_HTML.jpg

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