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重新考察在乳酸介质中作为绿色溶剂和催化剂合成 1,2,3,4-四取代吡咯衍生物。

Revisit to the synthesis of 1,2,3,4-tetrasubstituted pyrrole derivatives in lactic acid media as a green solvent and catalyst.

机构信息

Department of Chemistry, Art and Science Faculty, Cukurova University, Adana, Turkey.

Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Mersin University, Mersin, Turkey.

出版信息

Mol Divers. 2021 Nov;25(4):2321-2338. doi: 10.1007/s11030-020-10122-1. Epub 2020 Sep 27.

Abstract

In this study, for the first time, lactic acid was used as a bio-based green catalyst and reaction medium for the synthesis of 1,2,3,4-tetrasubstituted pyrrole derivatives from one-pot three-component reaction of commercially available primary amines, 1,3-dicarbonyl compounds, and trans-β-nitrostyrene at room temperature. Thirty-three corresponding pyrroles, of which eight are novel and have been reported for the first time, were synthesized in high to excellent yields in lactic acid media and characterized by spectroscopic analysis. In all examined cases, lactic acid represented many advantages, including shorter reaction time, ease of product isolation, higher yields, no by-products, no chromatographic process, and lower volatility in the reaction. This bio-based green solvent can also be recycled and reused three times without loss of its efficiency as a catalyst and solvent.

摘要

在这项研究中,乳酸首次被用作生物基绿色催化剂和反应介质,用于在室温下通过一锅法三组分反应,由商业可得的伯胺、1,3-二羰基化合物和反式-β-硝基苯乙烯合成 1,2,3,4-四取代吡咯衍生物。在乳酸介质中合成了 33 个相应的吡咯,其中 8 个是新型的,并且是首次报道。它们均通过光谱分析进行了表征。在所研究的所有情况下,乳酸都具有许多优点,包括反应时间更短、产物易于分离、产率更高、无副产物、无需色谱过程以及反应挥发性更低。这种生物基绿色溶剂还可以回收并重复使用三次,而不会降低其作为催化剂和溶剂的效率。

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