Organocatalyst 1,4-diazabicyclo [2.2.2]Octane (DABCO)-Catalyzed Sustainable Synthesis of Bis-Thiazolidinones Derivatives and their Spectral and DFT Analysis

IF 1.7 3区 化学 Q3 CHEMISTRY, ORGANIC Current Organic Chemistry Pub Date : 2024-04-17 DOI:10.2174/0113852728304587240319061348
Saloni Sahal, Mamta Chahar, Har Lal Singh, Renu Bishnoi, Sarita Khaturia
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Abstract

: Organocatalyst 1,4-diazabicyclo [2.2.2]octane (DABCO) has proven to be an efficient and environmentally friendly catalyst in the multicomponent reaction involving aldehydes, ethylenediamine, and thioglycolic acid under microwave conditions. DABCO stands out among other organic catalysts due to its costeffectiveness, non-toxic nature, and environmentally conscious profile. The method employed in this study exhibited exceptional attributes, such as high yields, swift reaction times, atom economy, catalyst reusability, and minimal catalyst loading. Additionally, there were excellent yields of products (90-94%). The melting points, UV-Vis, IR, 1HNMR, 13CNMR, were used to analyze the produced compounds. The in-vitro antibacterial activity of the synthesized compounds was investigated against pathogenic strains E. coli and Bacillus supstalis, and the results obtained were further explained with the help of DFT and molecular orbital calculations. Moreover, the compound 4b was found to be the most potent antibacterial agent amongst all tested compounds. result: Bis-thiazolidinones derivatives have been synthesized in excellent yields (90–94%) by mixing of aldehydes (2 mmol), ethylenediamine (1 mmol), thioglycolic acid (2 mmol), using DABCO (0.5 mmol), in 8 to 10 minutes under microwave irradiation.
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有机催化剂 1,4-二氮杂双环 [2.2.2]Octane (DABCO) 催化的双噻唑烷酮衍生物的可持续合成及其光谱和 DFT 分析
:有机催化剂 1,4-二氮杂双环[2.2.2]辛烷(DABCO)已被证明是一种高效、环保的催化剂,可用于微波条件下涉及醛、乙二胺和硫代乙醇酸的多组分反应。DABCO 因其成本效益高、无毒、环保等优点在众多有机催化剂中脱颖而出。本研究中采用的方法具有产量高、反应时间短、原子经济、催化剂可重复使用和催化剂负载最小等优异特性。此外,产品收率极高(90-94%)。利用熔点、紫外可见光、红外光谱、1HNMR 和 13CNMR 对生成的化合物进行了分析。在 DFT 和分子轨道计算的帮助下,研究了合成化合物对致病菌大肠杆菌和超级芽孢杆菌的体外抗菌活性。此外,还发现化合物 4b 是所有测试化合物中最有效的抗菌剂:在微波辐照下,将醛(2 毫摩尔)、乙二胺(1 毫摩尔)、巯基乙酸(2 毫摩尔)与 DABCO(0.5 毫摩尔)混合,在 8 至 10 分钟内合成了双噻唑烷酮衍生物,收率极高(90-94%)。
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来源期刊
Current Organic Chemistry
Current Organic Chemistry 化学-有机化学
CiteScore
3.70
自引率
7.70%
发文量
76
审稿时长
1 months
期刊介绍: Current Organic Chemistry aims to provide in-depth/mini reviews on the current progress in various fields related to organic chemistry including bioorganic chemistry, organo-metallic chemistry, asymmetric synthesis, heterocyclic chemistry, natural product chemistry, catalytic and green chemistry, suitable aspects of medicinal chemistry and polymer chemistry, as well as analytical methods in organic chemistry. The frontier reviews provide the current state of knowledge in these fields and are written by chosen experts who are internationally known for their eminent research contributions. The Journal also accepts high quality research papers focusing on hot topics, highlights and letters besides thematic issues in these fields. Current Organic Chemistry should prove to be of great interest to organic chemists in academia and industry, who wish to keep abreast with recent developments in key fields of organic chemistry.
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