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二水合氯化亚锡/氯化胆碱低共熔溶剂:在快速合成α-芳基乙酰胺和吲哚(吡咯并)[1,2-a]喹喔啉中的氧化还原性质

Tin(ii) chloride dihydrate/choline chloride deep eutectic solvent: redox properties in the fast synthesis of -arylacetamides and indolo(pyrrolo)[1,2-]quinoxalines.

作者信息

Trujillo Sergio Alfonso, Peña-Solórzano Diana, Bejarano Oscar Rodríguez, Ochoa-Puentes Cristian

机构信息

Laboratorio de Síntesis Orgánica Sostenible, Departamento de Química, Universidad Nacional de Colombia-Sede Bogotá Carrera 45 # 26-85 A.A. 5997 Bogotá Colombia

Laboratorio de Electroquímica y Termodinámica Computacional, Departamento de Química, Universidad Nacional de Colombia-Sede Bogotá Carrera 45 # 26-85 A.A. 5997 Bogotá Colombia.

出版信息

RSC Adv. 2020 Nov 6;10(66):40552-40561. doi: 10.1039/d0ra06871c. eCollection 2020 Nov 2.

Abstract

In this contribution a physicochemical, IR and Raman characterization for the tin(ii) chloride dihydrate/choline chloride eutectic mixture is reported. The redox properties of this solvent were also studied by cyclic voltammetry finding that it can be successfully used as an electrochemical solvent for electrosynthesis and electroanalytical processes and does not require negative potentials as verified by the reduction of nitrobenzene. The potential use of this eutectic mixture as a redox solvent was further explored in obtaining aromatic amines and -arylacetamides starting from a wide variety of nitroaromatic compounds. In addition, a fast synthetic strategy for the construction of a series of indolo(pyrrolo)[1,2-]quinoxalines was developed by reacting 1-(2-nitrophenyl)-1-indole(pyrrole) with aldehydes. This simple protocol offers a straightforward method for the construction of the target quinoxalines in short reaction times and high yields where the key step involves a tandem one-pot reductive cyclization-oxidation.

摘要

本文报道了二水合氯化亚锡/氯化胆碱低共熔混合物的物理化学、红外和拉曼表征。还通过循环伏安法研究了该溶剂的氧化还原性质,发现它可成功用作电合成和电分析过程的电化学溶剂,并且如通过硝基苯的还原所证实的那样,不需要负电位。在从多种硝基芳香化合物出发制备芳香胺和芳基乙酰胺的过程中,进一步探索了这种低共熔混合物作为氧化还原溶剂的潜在用途。此外,通过使1-(2-硝基苯基)-1-吲哚(吡咯)与醛反应,开发了一种快速合成一系列吲哚(吡咯并)[1,2-]喹喔啉的策略。这个简单的方案提供了一种直接的方法,可在短反应时间内以高收率构建目标喹喔啉,其中关键步骤涉及串联一锅法还原环化-氧化。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/be71/9057578/60ea800e969e/d0ra06871c-f1.jpg

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