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

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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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:
ionic liquid
synergistic activation
aminoethanol
2-oxazolidinone
atmospheric CO<sub>2</sub>
sustainable catalysis
Online Access:https://www.mdpi.com/1420-3049/23/11/3033
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spelling doaj-0b6dc1d39ffc4450a32a925d3f45cde62020-11-25T00:38:56ZengMDPI AGMolecules1420-30492018-11-012311303310.3390/molecules23113033molecules23113033Ionic Liquid-Promoted Three-Component Domino Reaction of Propargyl Alcohols, Carbon Dioxide and 2-Aminoethanols: A Thermodynamically Favorable Synthesis of 2-OxazolidinonesShumei Xia0Yu Song1Xuedong Li2Hongru Li3Liang-Nian He4State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, ChinaState Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, ChinaState Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, ChinaState Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, ChinaState Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, ChinaTo 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.https://www.mdpi.com/1420-3049/23/11/3033ionic liquidsynergistic activationaminoethanol2-oxazolidinoneatmospheric CO<sub>2</sub>sustainable catalysis
collection DOAJ
language English
format Article
sources DOAJ
author Shumei Xia
Yu Song
Xuedong Li
Hongru Li
Liang-Nian He
spellingShingle Shumei Xia
Yu Song
Xuedong Li
Hongru Li
Liang-Nian He
Ionic Liquid-Promoted Three-Component Domino Reaction of Propargyl Alcohols, Carbon Dioxide and 2-Aminoethanols: A Thermodynamically Favorable Synthesis of 2-Oxazolidinones
Molecules
ionic liquid
synergistic activation
aminoethanol
2-oxazolidinone
atmospheric CO<sub>2</sub>
sustainable catalysis
author_facet Shumei Xia
Yu Song
Xuedong Li
Hongru Li
Liang-Nian He
author_sort Shumei Xia
title Ionic Liquid-Promoted Three-Component Domino Reaction of Propargyl Alcohols, Carbon Dioxide and 2-Aminoethanols: A Thermodynamically Favorable Synthesis of 2-Oxazolidinones
title_short Ionic Liquid-Promoted Three-Component Domino Reaction of Propargyl Alcohols, Carbon Dioxide and 2-Aminoethanols: A Thermodynamically Favorable Synthesis of 2-Oxazolidinones
title_full Ionic Liquid-Promoted Three-Component Domino Reaction of Propargyl Alcohols, Carbon Dioxide and 2-Aminoethanols: A Thermodynamically Favorable Synthesis of 2-Oxazolidinones
title_fullStr Ionic Liquid-Promoted Three-Component Domino Reaction of Propargyl Alcohols, Carbon Dioxide and 2-Aminoethanols: A Thermodynamically Favorable Synthesis of 2-Oxazolidinones
title_full_unstemmed Ionic Liquid-Promoted Three-Component Domino Reaction of Propargyl Alcohols, Carbon Dioxide and 2-Aminoethanols: A Thermodynamically Favorable Synthesis of 2-Oxazolidinones
title_sort ionic liquid-promoted three-component domino reaction of propargyl alcohols, carbon dioxide and 2-aminoethanols: a thermodynamically favorable synthesis of 2-oxazolidinones
publisher MDPI AG
series Molecules
issn 1420-3049
publishDate 2018-11-01
description 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.
topic ionic liquid
synergistic activation
aminoethanol
2-oxazolidinone
atmospheric CO<sub>2</sub>
sustainable catalysis
url https://www.mdpi.com/1420-3049/23/11/3033
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AT yusong ionicliquidpromotedthreecomponentdominoreactionofpropargylalcoholscarbondioxideand2aminoethanolsathermodynamicallyfavorablesynthesisof2oxazolidinones
AT xuedongli ionicliquidpromotedthreecomponentdominoreactionofpropargylalcoholscarbondioxideand2aminoethanolsathermodynamicallyfavorablesynthesisof2oxazolidinones
AT hongruli ionicliquidpromotedthreecomponentdominoreactionofpropargylalcoholscarbondioxideand2aminoethanolsathermodynamicallyfavorablesynthesisof2oxazolidinones
AT liangnianhe ionicliquidpromotedthreecomponentdominoreactionofpropargylalcoholscarbondioxideand2aminoethanolsathermodynamicallyfavorablesynthesisof2oxazolidinones
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