Kit-6-NH2@Vanillin@α-亚甲基苯乙酮@吖啶- cu（ꟾ）可回收路易斯酸催化剂的合成及其在偶氮吖啶合成中的应用

IF 2.5 Q2 CHEMISTRY, MULTIDISCIPLINARY

Results in Chemistry Pub Date : 2025-04-14 DOI:10.1016/j.rechem.2025.102258

Leila Zare Fekri , Mohammad Nikpassand , Mogharab Torabi

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引用次数: 0

摘要

合成了Kit-6-NH2@Vanillin@ α-亚甲基苯乙酮@吖啶- cu（ꟾ）纳米粒子，并对其进行了表征。然后，研究了该新型纳米催化剂在二美酮、醛和4-氨基偶氮苯之间反应制备偶氮衍生二氢吡啶（吖啶）的应用。该工艺产率适宜，反应速度快。催化剂制备方便、分离简单、无溶剂条件下使用是该方案的主要优点。纳米催化剂可重复使用9次，催化效率无明显下降。1,4-二氢吡啶（DHP）衍生物用于药品和其他产品。在Hantsch法合成DHPs后，对该方法进行了各种改进，如在回流溶剂中使用不同的催化剂、超声辐照、微波条件和无溶剂程序。这些方法存在试剂复杂、溶剂消耗大、反应时间长、反应效率低等问题。虽然有些方法效果很好，但重要的是要找到一种更好的催化剂来制造1,4-二磷酸。方法将1 mmol 4-氨基偶氮苯、1 mmol乙醛、2 mmol二美酮和0.05 g催化剂混合，室温搅拌。采用薄层色谱法（4:1乙酸乙酯：正己烷）控制反应过程。在TLC监测所需的反应时间后，加入10ml热EtOH到混合物中。催化剂经过滤分离后可重复使用。本文首次报道了用Kit-6-NH2@Vanillin@α-亚甲基苯乙酮@吖啶- cu (I)合成偶氮偶联二氢吡啶的方法。与大多数报道的方法相比，更短的反应时间和更高的收率是本研究的两个主要优点。该反应在无溶剂条件下进行，不需要使用有机溶剂和有害溶剂。该反应是在室温下进行的，不需要加热，由于能源经济，它是基于绿色化学规则的。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Synthesis of new organic-inorganic hybride of Kit-6-NH2@Vanillin@α-methyleneacetophenone@ acridine-Cu(ꟾ) as a recoverable Lewis acid catalyst and its application for the synthesis of azoacridines

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Synthesis of new organic-inorganic hybride of Kit-6-NH2@Vanillin@α-methyleneacetophenone@ acridine-Cu(ꟾ) as a recoverable Lewis acid catalyst and its application for the synthesis of azoacridines

Kit-6-NH₂@Vanillin@ α-methyleneacetophenone @ acridine-Cu (ꟾ) nanoparticles were synthesized and were characterized completely. Then, the application of this new nano catalyst for the preparation of azo-derived dihydropyridines (acridines) via the treatment between dimedone, aldehydes, and 4-aminoazobenzene was investigated. The procedure proceeded in suitable yield and good reaction speed. Easy preparation of the catalyst, simple isolation and use of solvent-free condition are the main advantages of the protocol. The nanocatalyst can be reused for nine reaction cycles with no notable decrease in catalytic efficiency.

Background

1,4-Dihydropyridine (DHP) derivatives are used in medicines and other products. After Hantsch method for the synthesis of DHPs, various modifications were carried out on this method such as using different catalysts in refluxing solvent, under ultrasound irradiation, microwave condition, and solvent-free procedure. These methods suffer from many problems such as: use of complex reagents, high consumption of solvent, long time and in some cases low reaction efficiency. While some methods work well, it is important to find a better catalyst for making 1,4-DHPs.

Method

1 mmol of 4-aminoazobenzene, 1 mmol of aldehyde, 2 mmol of dimedone and 0.05 g of catalyst were mixed and was stirred at room temperature. The reaction progress was controlled by TLC (4:1 Ethylacetate:n-hexane). After required reaction time monitored by TLC, 10 mL of hot EtOH was added to mixture. The catalyst was separated by filtration and reused for successive run.

Key finding

This is the first report for the synthesis of azo-linked dihydropyridines using Kit-6-NH₂@Vanillin@α-methyleneacetophenone@ acridine-Cu(I). Shorter reaction time and higher yield rather than most of reported methods are two major benefits of this work. The reaction was carried out under solvent-free condition and there is no need to use organic and hazardous solvents in this procedure. The reaction was carried out at room temperature that need no heating and it is based on green chemistry rules because is energy-economical.

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