Hassanpour Hannaneh, Naeimi Hossein
Department of Organic Chemistry, Faculty of Chemistry, University of Kashan Kashan 87317-51167 I.R. Iran
RSC Adv. 2024 May 29;14(24):17296-17305. doi: 10.1039/d3ra08705k. eCollection 2024 May 22.
This study presents a description of the catalytic synthesis of indeno[1,2-]indolone derivatives. In this method, initially, a Schiff base compound was synthesized from the reaction of acetylacetone with 2-hydroxyaniline. Then, the prepared Schiff base was immobilized on chelated magnetic copper ferrite nanoparticles with a chitosan surface to design and prepare the CuFeO@CS-SB nanocomposite. Further, the one-pot multi-component cyclization reaction of aniline, dimedone and ninhydrin was conducted using the synthesized nanocomposite as a heterogeneous acid catalyst in water solvent under thermal conditions. In this reaction, the products were obtained in excellent yields and short reaction times, and the catalyst could be recycled and reused six times without any loss in product yields. By conducting FT-IR spectroscopy, H NMR spectroscopy, XRD, FE-SEM, TGA, elemental mapping scanning, EDX and BET analyses, the structure of the nanocatalyst was characterized. In addition, for the identification of organic compounds, FT-IR, H NMR, and C NMR spectroscopies and melting point analysis were used, which confirmed the synthesis of this class of derivatives.
本研究描述了茚并[1,2 - ]吲哚酮衍生物的催化合成。在该方法中,首先,乙酰丙酮与2 - 羟基苯胺反应合成了一种席夫碱化合物。然后,将制备的席夫碱固定在具有壳聚糖表面的螯合磁性铜铁氧体纳米颗粒上,以设计并制备CuFeO@CS - SB纳米复合材料。此外,以合成的纳米复合材料作为多相酸催化剂,在水溶剂中于热条件下进行苯胺、二氢黄酮和茚三酮的一锅多组分环化反应。在该反应中,产物以优异的产率和较短的反应时间得到,并且催化剂可以循环使用六次而产物产率没有任何损失。通过傅里叶变换红外光谱(FT - IR)、氢核磁共振光谱(¹H NMR)、X射线衍射(XRD)、场发射扫描电子显微镜(FE - SEM)、热重分析(TGA)、元素映射扫描、能谱分析(EDX)和比表面积分析(BET)对纳米催化剂的结构进行了表征。此外,使用傅里叶变换红外光谱(FT - IR)、氢核磁共振光谱(¹H NMR)、碳核磁共振光谱(¹³C NMR)和熔点分析来鉴定有机化合物,这证实了此类衍生物的合成。