一种新型强效氯化胆碱-硫脲/硫酸催化剂,高效可回收,微波辅助合成喹唑啉- 4(3H) - 1衍生物作为绿色介质抗菌剂

IF 0.9 Q4 CHEMISTRY, MULTIDISCIPLINARY
F. Norouzi, N. Foroughifar, A. Khajeh-Amiri, H. Pasdar
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引用次数: 0

摘要

氯化胆碱-硫脲/硫酸是一种强力高效的绿色催化剂,用于在微波辐射和无溶剂条件下,通过多种胺、乙酸酐和邻氨基苯酸的反应,一锅合成喹唑啉-4 (3H) - 1衍生物(4a-q)。微波辐射是一种比传统加热更快、更经济、更节能、更有效的方法,已被用于合成一些喹唑啉酮衍生物。近十年来,绿色合成是合成有机化学的一个重要研究方向,即利用高效、环保的方法合成生物化合物。使用催化剂具有显著的优势,包括易于制备和分离,化学和热稳定性,以及可重复使用,低成本,高效,易于处理技术等环境友好性。因此,按照绿色化学和最少废弃物的原则,采用能量和化学反应物最少的无毒有机催化剂来实现该机理。采用一锅法和顺序加成法合成了喹唑啉酮衍生物。在顺序加成法中,首先在微波照射下向反应容器中加入乙酸酐和邻苯甲酸,然后加入氯化胆碱硫脲/硫酸作为高效可回收的绿色催化剂和所需的胺。采用孔扩散法对不同病原菌进行体外抑菌活性评价。病原菌为白色念珠菌ATCC 10231(酵母菌)、黑曲霉ATCC 16404(真菌)、大肠杆菌ATCC 8739、铜绿假单胞菌ATCC 9027(细菌)和ATCC 6538、表皮金黄色葡萄球菌ATCC 12228。含有3-羟基、2,5-二甲氧基、4-溴、4-甲氧基和4-氯基团连接在嘧啶苯环上的含嘧啶化合物具有抗菌性能。在较短的反应时间内,以高效率合成了多种具有生物活性的喹唑啉酮衍生物。结果表明,以脂肪族胺为原料,反应时间短,反应效率高。芳香族胺合成的产品具有更好的抗菌性能。本研究以chcl -硫脲/ H2SO4为催化剂,在微波辐射和无溶剂条件下合成了多种2-甲基-喹唑啉-4 (3H) - 1衍生物(4a-q),作为高效、环保、可回收的催化剂。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
A novel powerful Choline Chloride – Thiourea /Sulfuric Acid, efficient and recyclable catalyst via microwave‐assisted for the synthesis of Quinazolin- 4(3H)–one derivatives as Antibacterial Agents in green media
Choline Chloride - Thiourea / Sulfuric Acid is a powerful and efficient green catalyst used for one-pot synthesis of quinazoline-4 (3H) -one derivatives via a reaction between various amines, acetic anhydride, and anthranilic acid under microwave irradiation and solvent-free conditions (4a-q). Microwave irradiation, which is a faster, more cost-effective, less energy-intensive, and more efficient method than conventional heating, has been used to synthesize some quinazolinone derivatives. For the past ten years, one of the major subjects in synthetic organic chemistry has been green synthesis, which has used efficient and environmentally friendly methods to synthesize biological compounds. The use of catalysts has significant advantages, including ease of preparation and separation, chemical and thermal stability, and environmental friendliness due to features such as reusability, low cost, and efficient, easy workup techniques. Therefore, the mechanism is performed by a non-toxic organic catalyst that uses the least energy and chemical reactants in accordance with the principles of green chemistry and least waste. One-pot and sequential addition methods have been used to synthesize quinazolinone derivatives. In the sequential addition method, the reaction was started by adding acetic anhydride and anthranilic acid to the reaction vessel under microwave irradiation and continued by adding choline chloride thiourea / sulfuric acid as efficient recyclable green catalysts and the desired amine. In vitro, the well diffusion method against different pathogenic strains was used to evaluate the antimicrobial activity of quinazoline-4 (3H) -one derivatives. Pathogenic strains used were Candida albicans ATCC 10231 (yeast), Aspergillus niger ATCC 16404 (fungus), Escherichia coli ATCC 8739, Pseudomonas aeruginosa ATCC 9027 (bacteria) and ATCC 6538, and Staphylococcus aureus S. epidermidis ATCC 12228. Pyrimidine-containing compounds in which the 3-hydroxyl, 2,5-Dimethoxy, 4-bromo, 4 ‐ Methoxy, and 4 ‐ chloro groups are attached to the phenyl ring of pyrimidine exhibit antimicrobial properties. In a short reaction time, a variety of biologically active quinazolinone derivatives were synthesized with a high efficiency. According to the results, it was found that with aliphatic amines, the reaction time was shorter and the reaction efficiency was higher. Products synthesized from aromatic amines had more antibacterial properties. In this work, a variety of 2-methyl-quinazoline-4 (3H) -one derivatives (4a–q) were synthesized as potent antibacterial agents under microwave irradiation and solvent-free conditions in the presence of ChCl-thiourea / H2SO4 as an efficient, eco-friendly, and recyclable catalyst.
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Current Microwave Chemistry
Current Microwave Chemistry CHEMISTRY, MULTIDISCIPLINARY-
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