Ionic Liquid-Promoted Three-Component Domino Reaction of Propargyl Alcohols, Carbon Dioxide and 2-Aminoethanols: A Thermodynamically Favorable Synthesis of 2-Oxazolidinones

To circumvent the thermodynamic limitation of the synthesis of oxazolidinones starting from 2-aminoethanols and CO<sub>2</sub> and realize incorporation CO<sub>2</sub> under atmospheric pressure, a protic ionic liquid-facilitated three-component reaction of propargyl alcohols...

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Bibliographic Details
Main Authors: Shumei Xia, Yu Song, Xuedong Li, Hongru Li, Liang-Nian He
Format: Article
Language:English
Published: MDPI AG 2018-11-01
Series:Molecules
Subjects:
Online Access:https://www.mdpi.com/1420-3049/23/11/3033
Description
Summary:To circumvent the thermodynamic limitation of the synthesis of oxazolidinones starting from 2-aminoethanols and CO<sub>2</sub> and realize incorporation CO<sub>2</sub> under atmospheric pressure, a protic ionic liquid-facilitated three-component reaction of propargyl alcohols, CO<sub>2</sub> and 2-aminoethanols was developed to produce 2-oxazolidinones along with equal amount of &#945;-hydroxyl ketones. The ionic liquid structure, reaction temperature and reaction time were in detail investigated. And 15 mol% 1,5,7-triazabicylo[4.4.0]dec-5-ene ([TBDH][TFE]) trifluoroethanol was found to be able to synergistically activate the substrate and CO<sub>2</sub>, thus catalyzing this cascade reaction under atmospheric CO<sub>2</sub> pressure. By employing this task-specific ionic liquid as sustainable catalyst, 2-aminoethanols with different substituents were successfully transformed to 2-oxazolidinones with moderate to excellent yield after 12 h at 80 &#176;C.
ISSN:1420-3049