[BPy][OH]固定化水滑石-粘土催化体系合成1,2-二氢喹唑啉

IF 0.9 Q4 CHEMISTRY, PHYSICAL Current Organocatalysis Pub Date : 2023-07-26 DOI:10.2174/2213337210666230726123919
V. Srivastava
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Overall, the use of hydrotalcite and [BPy][OH] catalysts provide a more efficient and environmentally friendly method for synthesizing quinazolines compared to traditional methods that often require harsh conditions and toxic reagents.\n\n\n\n1,2-Dihydroquinazolines are an important class of heterocyclic compounds with diverse biological activities, including anticancer, antifungal, and antibacterial properties. They also exhibit other pharmacological activities such as antihypertensive, anti-inflammatory, and antiviral effects. The synthesis of 1,2-dihydroquinazolines dates to the early 20th century when they were first synthesized by Pictet and Huber in 1911 by the condensation of anthranilic acid with aldehydes or ketones in the presence of strong acids. Since then, numerous methods have been developed for their synthesis, including the cyclization of o-aminobenzamides, the reaction of o-aminoaryl ketones with aldehydes or ketones, and the use of catalysts such as Lewis acids and transition metals. In recent years, the development of new synthetic methods for the efficient and selective synthesis of 1,2-dihydroquinazolines has been of great interest to synthetic chemists, particularly in the pharmaceutical industry. These methods include the use of microwave irradiation, ultrasound, and ionic liquids as green solvents. \nOverall, the synthesis of 1,2-dihydroquinazolines has been an active area of research, and new methods continue to be developed to improve their synthesis and properties for various applications.\n\n\n\nWe easily synthesized two ionic liquids, [BMIM][OH] and [BPy][OH], with high yields. 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引用次数: 0

摘要

我们简单地合成了[BMIM][OH]和[BPy][OH]两种离子液体,产率高。我们发现这些离子液体介导的水滑石粘土是合成具有生物活性的1,2-二氢喹唑啉衍生物的高效催化剂。利用简单的反应方案和简单的产物分离步骤,我们成功地合成了18种不同的1,2-二氢喹唑啉衍生物,并且催化剂的循环利用率高达8次。总的来说,与通常需要恶劣条件和有毒试剂的传统方法相比,使用水滑石和[BPy][OH]催化剂为合成喹唑啉提供了一种更高效、更环保的方法。1,2-二氢喹唑啉类化合物是一类重要的杂环化合物,具有抗癌、抗真菌和抗菌等多种生物活性。它们还具有其他药理活性,如抗高血压、抗炎和抗病毒作用。1,2-二氢喹唑啉的合成可以追溯到20世纪初,当时Pictet和Huber在1911年通过在强酸存在下将邻氨基苯甲酸与醛或酮缩合而首次合成了它们。从那时起,已经开发了许多方法来合成它们,包括邻氨基苯酰胺的环化,邻氨基芳基酮与醛或酮的反应,以及使用催化剂,如路易斯酸和过渡金属。近年来,高效、选择性合成1,2-二氢喹唑啉类化合物的新合成方法的发展引起了合成化学家的极大兴趣,特别是在制药工业中。这些方法包括使用微波辐照、超声波和离子液体作为绿色溶剂。总的来说,1,2-二氢喹唑啉的合成一直是一个活跃的研究领域,新的方法不断被开发出来,以改进它们的合成和性能,以实现各种应用。我们简单地合成了[BMIM][OH]和[BPy][OH]两种离子液体,产率高。我们发现这些离子液体介导的水滑石粘土是合成具有生物活性的1,2-二氢喹唑啉衍生物的高效催化剂。总的来说,我们的结果为开发高效和可持续的合成1,2 -二氢喹唑啉的方法提供了见解。综上所述,我们的研究表明,[BPy][OH]离子液体和水滑石粘土催化体系可以用不同的芳香羰基化合物、氨基苯甲酮衍生物和杂环醛合成各种1,2 -二氢喹唑啉。在苯基上存在供电子取代基比吸电子取代基的产率更高,醛基的对位比邻位或间位的影响更显著。我们的催化系统也被发现是可回收的多达八次运行,没有显著的催化活性损失。总的来说,我们的结果为开发高效和可持续的合成1,2 -二氢喹唑啉的方法提供了见解。
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[BPy][OH] Immobilized Hydrotalcite Clay Catalytic System for 1,2-dihydroquinazolines Synthesis
We easily synthesized two ionic liquids, [BMIM][OH] and [BPy][OH], with high yield. We found that hydrotalcite clay, mediated by these ionic liquids, is a highly effective catalyst for synthesizing biologically active 1,2-dihydroquinazoline derivatives. Using a simple reaction protocol and easy product isolation steps, we successfully synthesized 18 different 1,2-dihydroquinazoline derivatives and were able to recycle the catalysts up to 8 times. Overall, the use of hydrotalcite and [BPy][OH] catalysts provide a more efficient and environmentally friendly method for synthesizing quinazolines compared to traditional methods that often require harsh conditions and toxic reagents. 1,2-Dihydroquinazolines are an important class of heterocyclic compounds with diverse biological activities, including anticancer, antifungal, and antibacterial properties. They also exhibit other pharmacological activities such as antihypertensive, anti-inflammatory, and antiviral effects. The synthesis of 1,2-dihydroquinazolines dates to the early 20th century when they were first synthesized by Pictet and Huber in 1911 by the condensation of anthranilic acid with aldehydes or ketones in the presence of strong acids. Since then, numerous methods have been developed for their synthesis, including the cyclization of o-aminobenzamides, the reaction of o-aminoaryl ketones with aldehydes or ketones, and the use of catalysts such as Lewis acids and transition metals. In recent years, the development of new synthetic methods for the efficient and selective synthesis of 1,2-dihydroquinazolines has been of great interest to synthetic chemists, particularly in the pharmaceutical industry. These methods include the use of microwave irradiation, ultrasound, and ionic liquids as green solvents. Overall, the synthesis of 1,2-dihydroquinazolines has been an active area of research, and new methods continue to be developed to improve their synthesis and properties for various applications. We easily synthesized two ionic liquids, [BMIM][OH] and [BPy][OH], with high yields. We found that hydrotalcite clay, mediated by these ionic liquids, is a highly effective catalyst for synthesizing biologically active 1,2-dihydroquinazoline derivatives. Overall, our results provide insights into the development of efficient and sustainable methods for the synthesis of 1, 2-dihydroquinazolines. In summary, our studies demonstrated that the [BPy][OH] ionic liquid and hydrotalcite clay catalytic system could be used for the synthesis of various 1, 2-dihydroquinazolines using different aromatic carbonyl compounds, amino benzophenone derivatives, and heterocyclic aldehydes. The presence of electron-donating substituents in the phenyl group provided higher yields than electron-withdrawing groups, and the para position of the aldehyde group had a more significant effect than the ortho or meta position. Our catalytic system was also found to be recyclable for up to eight runs without significant loss of catalytic activity. Overall, our results provide insights into the development of efficient and sustainable methods for the synthesis of 1, 2-dihydroquinazolines.
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来源期刊
Current Organocatalysis
Current Organocatalysis CHEMISTRY, PHYSICAL-
CiteScore
2.00
自引率
0.00%
发文量
28
期刊介绍: Current Organocatalysis is an international peer-reviewed journal that publishes significant research in all areas of organocatalysis. The journal covers organo homogeneous/heterogeneous catalysis, innovative mechanistic studies and kinetics of organocatalytic processes focusing on practical, theoretical and computational aspects. It also includes potential applications of organocatalysts in the fields of drug discovery, synthesis of novel molecules, synthetic method development, green chemistry and chemoenzymatic reactions. This journal also accepts papers on methods, reagents, and mechanism of a synthetic process and technology pertaining to chemistry. Moreover, this journal features full-length/mini review articles within organocatalysis and synthetic chemistry. It is the premier source of organocatalysis and synthetic methods related information for chemists, biologists and engineers pursuing research in industry and academia.
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