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Article

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

1
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China
2
College of Pharmacy, Nankai University, Tianjin 300353, China
*
Authors to whom correspondence should be addressed.
Molecules 2018, 23(11), 3033; https://doi.org/10.3390/molecules23113033
Received: 15 October 2018 / Revised: 19 November 2018 / Accepted: 20 November 2018 / Published: 20 November 2018
(This article belongs to the Special Issue Sustainable Synthesis)
To circumvent the thermodynamic limitation of the synthesis of oxazolidinones starting from 2-aminoethanols and CO2 and realize incorporation CO2 under atmospheric pressure, a protic ionic liquid-facilitated three-component reaction of propargyl alcohols, CO2 and 2-aminoethanols was developed to produce 2-oxazolidinones along with equal amount of α-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 CO2, thus catalyzing this cascade reaction under atmospheric CO2 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 °C. View Full-Text
Keywords: ionic liquid; synergistic activation; aminoethanol; 2-oxazolidinone; atmospheric CO2; sustainable catalysis ionic liquid; synergistic activation; aminoethanol; 2-oxazolidinone; atmospheric CO2; sustainable catalysis
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MDPI and ACS Style

Xia, S.; Song, Y.; Li, X.; Li, H.; He, L.-N. Ionic Liquid-Promoted Three-Component Domino Reaction of Propargyl Alcohols, Carbon Dioxide and 2-Aminoethanols: A Thermodynamically Favorable Synthesis of 2-Oxazolidinones. Molecules 2018, 23, 3033. https://doi.org/10.3390/molecules23113033

AMA Style

Xia S, Song Y, Li X, Li H, He L-N. Ionic Liquid-Promoted Three-Component Domino Reaction of Propargyl Alcohols, Carbon Dioxide and 2-Aminoethanols: A Thermodynamically Favorable Synthesis of 2-Oxazolidinones. Molecules. 2018; 23(11):3033. https://doi.org/10.3390/molecules23113033

Chicago/Turabian Style

Xia, Shumei, Yu Song, Xuedong Li, Hongru Li, and Liang-Nian He. 2018. "Ionic Liquid-Promoted Three-Component Domino Reaction of Propargyl Alcohols, Carbon Dioxide and 2-Aminoethanols: A Thermodynamically Favorable Synthesis of 2-Oxazolidinones" Molecules 23, no. 11: 3033. https://doi.org/10.3390/molecules23113033

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