Lignin-derived Brønsted acidic catalyst for the green synthesis of biologically relevant indole derivatives

IF 1.7 4区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Journal of Chemical Sciences Pub Date : 2024-10-25 DOI:10.1007/s12039-024-02315-0
Balasubramaniyam Manikandan, Balasubramanian Indrajit Karikalan, Padmaja Gopal, Vaishanya Moorthy, Supriyo Chakraborty, Subramaniapillai Selva Ganesan
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Abstract

Readily available, naturally derived lignin was transformed into a Brønsted acidic organocatalyst. The obtained catalyst was utilized in the environmentally benign synthesis of biologically relevant indole derivatives such as vibrindole, turbomycin, etc. The scope of the developed methodology was further extended for the synthesis of aniline-tethered indoles, 4H-chromene, and indolin-2-one derivatives. Further, vicinal difunctionalization was successfully carried out with the aid of the developed organocatalyst. Imperatively, all the aforementioned reactions were carried out in the aqueous medium. The reusability of the heterogeneous catalyst was also proved by carrying out the reaction with the recovered catalyst.

Graphical abstract

Lignin-based naturally derived Brønsted acidic organocatalyst was utilized in the environmentally benign synthesis of biologically relevant indole derivatives, 4H-chromene, and indolin-2-one derivatives. All the aforementioned transformations were carried out in an environmentally benign aqueous medium.

Abstract Image

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用于绿色合成生物相关吲哚衍生物的木质素衍生布氏酸催化剂
现成的天然木质素被转化为一种布氏酸性有机催化剂。所获得的催化剂被用于合成与生物相关的吲哚衍生物,如振动吲哚、多波霉素等,对环境无害。所开发方法的范围进一步扩展到苯胺系吲哚、4H-色烯和吲哚啉-2-酮衍生物的合成。此外,在所开发的有机催化剂的帮助下,还成功地进行了邻位双官能化。更重要的是,上述所有反应都是在水介质中进行的。通过使用回收的催化剂进行反应,也证明了该异相催化剂的可重复使用性。图解摘要利用基于木质素的天然衍生布氏酸性有机催化剂合成了与生物相关的吲哚衍生物、4H-色烯和吲哚啉-2-酮衍生物,对环境无害。上述所有转化过程均在对环境无害的水介质中进行。
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来源期刊
Journal of Chemical Sciences
Journal of Chemical Sciences CHEMISTRY, MULTIDISCIPLINARY-
CiteScore
3.10
自引率
5.90%
发文量
107
审稿时长
1 months
期刊介绍: Journal of Chemical Sciences is a monthly journal published by the Indian Academy of Sciences. It formed part of the original Proceedings of the Indian Academy of Sciences – Part A, started by the Nobel Laureate Prof C V Raman in 1934, that was split in 1978 into three separate journals. It was renamed as Journal of Chemical Sciences in 2004. The journal publishes original research articles and rapid communications, covering all areas of chemical sciences. A significant feature of the journal is its special issues, brought out from time to time, devoted to conference symposia/proceedings in frontier areas of the subject, held not only in India but also in other countries.
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