On-water Catalyst-free Synthesis of 3-Alkenyl Oxindoles

Kumarasinghe K.G.U.R., Samaradiwakara D.M.T.A.
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Abstract

3-Alkenyl oxindoles are key structural motifs in organic chemistry with a wide range of applications mainly in the pharmaceutical industry, due to excellent biological activities such as anti-inflammatory, antiviral, antibacterial, and anticancer properties. With the discovery of the importance of oxindole derivatives in the pharmaceutical industry, demand for sustainable protocols for the synthesis increased as most classical methods have their limitations and flaws. In this study on-water, catalyst-free, atom-economical green approach was developed for the synthesis of 3- alkenyl oxindole derivatives using oxindole and aldehyde as starting materials. The reaction between oxindole and benzaldehyde was conducted on water under catalyst-free conditions. Interestingly, 100% conversion was observed when the reaction was carried out for 24 hours at 100° C. As the next step, the applicability of the developed approach was proven for different aldehydes. Furaldehyde, cinnamaldehyde, and vanillin were used as the aldehydes to synthesize 3- alkenyl oxindole derivatives, and the isolated yields were obtained as 77%, 54%, and 51% respectively. The desired product formation was confirmed by comparing the Rf value of the product with that of the previously synthesized well-characterized compounds; 3- benzylideneindolin-2-one, 3-(furan-3-methylene)indolin-2-one, 3-(3-phenylallylidene)indolin-2- one, and 3-(4-hydroxy-3-methoxybenzylidene)indolin-2-one using Thin Layer Chromatography. Further characterization was done by Fourier-transform infrared (FT-IR), Ultraviolet-visible (UVVis), and Nuclear Magnetic Resonance (NMR) spectroscopic techniques. In further optimization steps, the reaction was performed using surfactants as the catalyst. By adhering to the green chemistry principles different sources of biosurfactants were used including Acacia concinna pods, Sapindus emarginatus fruit pericarp, Dillenia retusa fruit pericarp, and Trigonella foenumgraecum seeds. In order to compare the effect of biosurfactants, a synthetic surfactant, sodium dodecyl sulfate (SDS) was used as the catalyst. When the reaction was carried out for 21 hours at 100 °C using fruit pericarp of Sapindus emarginatus as the source of biosurfactant, 100% conversion was observed. Using water as the solvent, readily available starting materials, higher yield, and eco-friendliness and catalyst-free conditions suggest the possible use of the developed method for large-scale preparations of 3-alkenyl oxindole derivatives. Keywords: Green protocol, Oxindole derivatives, Surfactant, On water synthesis, Catalyst-free
无水催化剂合成 3-烯基羰基吲哚
3-Alkenyl oxindoles 是有机化学中的关键结构基团,由于具有抗炎、抗病毒、抗菌和抗癌等优异的生物活性,主要在制药行业有着广泛的应用。随着人们发现吲哚衍生物在制药业中的重要性,对可持续合成方案的需求也随之增加,因为大多数经典方法都有其局限性和缺陷。本研究以吲哚和醛为起始原料,开发了水上、无催化剂、原子经济的绿色方法来合成 3-烯基吲哚衍生物。在无催化剂条件下,吲哚和苯甲醛在水中发生反应。有趣的是,当反应在 100 摄氏度下进行 24 小时时,观察到了 100% 的转化率。呋喃醛、肉桂醛和香兰素被用作合成 3-烯基吲哚衍生物的醛,其分离产率分别为 77%、54% 和 51%。利用薄层色谱法,将产物的 Rf 值与之前合成的特征良好的化合物(3-亚苄基吲哚啉-2-酮、3-(呋喃-3-亚甲基)吲哚啉-2-酮、3-(3-苯基亚烯丙基)吲哚啉-2-酮和 3-(4-羟基-3-甲氧基亚苄基)吲哚啉-2-酮)的 Rf 值进行比较,确认了所需产物的形成。傅立叶变换红外光谱(FT-IR)、紫外可见光光谱(UVVis)和核磁共振光谱(NMR)技术对其进行了进一步表征。在进一步优化步骤中,使用表面活性剂作为催化剂进行了反应。根据绿色化学原则,使用了不同来源的生物表面活性剂,包括金合欢豆荚、无患子果皮、莳萝果皮和三叶草种子。为了比较生物表面活性剂的效果,使用了合成表面活性剂十二烷基硫酸钠(SDS)作为催化剂。使用无患子果皮作为生物表面活性剂来源,在 100 °C 下进行 21 小时的反应,观察到 100%的转化率。以水为溶剂、易得的起始原料、较高的产率、生态友好性和无催化剂条件表明,所开发的方法可用于大规模制备 3-烯基吲哚衍生物。关键词绿色方案 氧化吲哚衍生物 表面活性剂 水上合成 无催化剂
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