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Ionic Liquid-Promoted Three-Component Domino Reaction of Propargyl Alcohols, Carbon Dioxide and 2-Aminoethanols: A Thermodynamically Favorable Synthesis of 2-Oxazolidinones
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. Molecules2018, 23, 3033.
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.
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. Molecules2018, 23, 3033.
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.
Abstract
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% [TBDH][TFE] (1,5,7-triazabicylo[4.4.0]dec-5-ene 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 oC. This three-component reaction running under atmospheric pressure proves to be a clever detour to avoid the thermodynamic issue in the synthesis of 2-oxazolidinones starting from 2-aminoethanols and CO2.
Chemistry and Materials Science, Organic Chemistry
Copyright:
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
The commenter has declared there is no conflict of interests.
Comment:
This article provides a novel route of ionic liquid-promoted three-component reaction of propargyl alcohols, CO2 and 2-aminoethanols, to synthesize both 2-oxazolidinones and α-hydroxyl ketones under mild conditions, which tactfully circumvents the thermodynamic limitation in the conventional approach using 2-aminoethanols and CO2. This work has been reported in a systematic and detailed way, with clear and novel thinking, strong readability and beautiful figures and schemes.
Commenter:
The commenter has declared there is no conflict of interests.