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以柠檬汁为可再生资源,在聚光太阳辐射下合成2-芳基/杂芳基取代的2,3-二氢喹唑啉-4(1)-酮的绿色化学方法。

Green chemistry approach to the synthesis of 2-aryl/heteroaryl substituted 2,3-dihydroquinazolin-4(1)-ones using lemon juice under concentrated solar radiations as a renewable source.

作者信息

Khan Rehana A, Adole Vishnu A, Pawar Thansing B, Jagdale Bapu S

机构信息

Department of Chemistry, Mahatma Gandhi Vidyamandir's Loknete Vyankatrao Hiray Arts, Science and Commerce College Panchavati Nashik 422003 MS India

出版信息

RSC Adv. 2024 Oct 14;14(44):32350-32357. doi: 10.1039/d4ra05772d. eCollection 2024 Oct 9.

Abstract

This study explores a novel and eco-friendly synthesis of 22 derivatives of 2-aryl/heteroaryl substituted 2,3-dihydroquinazolin-4(1)-ones, compounds with significant medicinal potential, using concentrated solar radiation (CSR) and lemon juice as a natural catalyst. Traditional methods for synthesizing these compounds often involve complex, energy-intensive processes and toxic reagents. In contrast, the method presented here utilizes solar energy and a biodegradable, non-toxic catalyst, aligning with the principles of green chemistry. The reaction, involving 2-aminobenzamide and various aromatic and heteroaromatic aldehydes, was optimized by varying temperature, catalyst concentration, and solvent. Through optimization, a combination of 0.3 mL of lemon juice and CSR achieved a 97% product yield in 10 minutes. A wide range of aromatic and heteroaromatic aldehydes were tested, all of which produced excellent yields, confirming the method's broad applicability. The substrate scope was explored with different aldehydes, containing groups/structures like chloro, bromo, nitro, methyl, methoxy, fluoro, hydroxy, imidazole, thiazole, chromone, pyrrole, and 1,4-dioxane, yielding up to 97%. Comparative studies with other catalysts and solvents confirmed the superior efficiency of lemon juice. This study not only demonstrates a sustainable approach to synthesizing 2,3-dihydroquinazolin-4(1)-ones but also highlights the potential of solar energy in organic synthesis, offering a viable alternative to conventional methods. This environmentally benign method offers an efficient and sustainable route for synthesizing 2,3-dihydroquinazolin-4(1)-one derivatives.

摘要

本研究探索了一种新型且环保的方法来合成22种2-芳基/杂芳基取代的2,3-二氢喹唑啉-4(1)-酮衍生物,这些化合物具有显著的药用潜力。该方法使用聚光太阳能辐射(CSR)和柠檬汁作为天然催化剂。传统的合成这些化合物的方法通常涉及复杂、耗能的过程以及有毒试剂。相比之下,本文提出的方法利用太阳能以及一种可生物降解的无毒催化剂,符合绿色化学的原则。该反应涉及2-氨基苯甲酰胺与各种芳香族和杂芳香族醛,通过改变温度、催化剂浓度和溶剂进行了优化。通过优化,0.3 mL柠檬汁与聚光太阳能辐射相结合,在10分钟内实现了97%的产物产率。测试了多种芳香族和杂芳香族醛,所有这些醛都产生了优异的产率,证实了该方法的广泛适用性。用不同的醛探索了底物范围,这些醛含有氯、溴、硝基、甲基、甲氧基、氟、羟基、咪唑、噻唑、色酮、吡咯和1,4-二氧六环等基团/结构,产率高达97%。与其他催化剂和溶剂的对比研究证实了柠檬汁的卓越效率。本研究不仅展示了一种可持续的合成2,3-二氢喹唑啉-4(1)-酮的方法,还突出了太阳能在有机合成中的潜力,为传统方法提供了一种可行的替代方案。这种环境友好型方法为合成2,3-二氢喹唑啉-4(1)-酮衍生物提供了一条高效且可持续的途径。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a7bd/11472284/2a585161fe0d/d4ra05772d-s1.jpg

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