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基于深共熔溶剂(DES)介导的一锅多组分绿色方法合成萘二甲酰亚胺基吖啶-1,8-二酮衍生物及其光物理性质

Deep Eutectic Solvent (DES)-Mediated One-Pot Multicomponent Green Approach for Naphthalimide-Centered Acridine-1,8-dione Derivatives and Their Photophysical Properties.

作者信息

Rather Ishfaq Ahmad, Alotaibi Saad H, Alotaibi Mohammed T, Altaf Mohammad, Ali Rashid

机构信息

Organic and Supramolecular Functional Materials Research Laboratory, Department of Chemistry, Jamia Millia Islamia, Jamia Nagar, Okhla, New Delhi 110025, India.

Department of Chemistry, Turabah University College, Taif University, P.O. Box 11099, Taif 21944, Saudi Arabia.

出版信息

ACS Omega. 2022 Sep 26;7(40):35825-35833. doi: 10.1021/acsomega.2c04026. eCollection 2022 Oct 11.

Abstract

An efficient and green methodology to assemble various functionalized naphthalimide-centered acridine-1,8-dione derivatives involving a one-pot multicomponent protocol has successfully been developed. Herein, a variety of aromatic aldehydes, 1,3-diketones, 1,8-naphthanoic anhydride, and hydrazine hydrate have been condensed under a reusable, inexpensive, and biodegradable deep eutectic solvent (DES) of 'dimethyl urea and l-(+)-tartaric acid to obtain the desired targets under operationally mild reaction conditions with outstanding conversions. Strikingly, in this strategy, the DES plays a dual role of a catalyst and solvent and was recycled efficiently in four consecutive runs with no substantial drop in the yield of the desired product. Interestingly, the easy recovery and high reusability of the DES make this simple yet efficient protocol environmentally desirable. Moreover, the preliminary photophysical properties of thus-prepared valuable molecules have also been investigated by ultraviolet-visible (UV-vis) and fluorescence spectroscopy.

摘要

一种高效且绿色的方法成功开发出来,该方法通过一锅多组分反应合成各种以功能化萘二甲酰亚胺为中心的吖啶-1,8-二酮衍生物。在此,多种芳香醛、1,3-二酮、1,8-萘二甲酸酐和水合肼在一种可重复使用、价格低廉且可生物降解的由二甲基脲和L-(+)-酒石酸组成的低共熔溶剂(DES)中缩合,在温和的反应条件下以出色的转化率得到所需产物。引人注目的是,在该策略中,DES起到了催化剂和溶剂的双重作用,并且在连续四次运行中能够高效回收利用,所需产物的产率没有大幅下降。有趣的是,DES易于回收且可高度重复使用,使得这个简单而高效的方法在环境方面具有优势。此外,还通过紫外可见(UV-vis)光谱和荧光光谱对如此制备的有价值分子的初步光物理性质进行了研究。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9ead/9558244/e20fc8739472/ao2c04026_0002.jpg

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