Preprint Article Version 1 This version is not peer-reviewed

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

Version 1 : Received: 15 October 2018 / Approved: 16 October 2018 / Online: 16 October 2018 (10:48:43 CEST)

A peer-reviewed article of this Preprint also exists.

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. Molecules 2018, 23, 3033.

Journal reference: Molecules 2018, 23, 3033
DOI: 10.3390/molecules23113033

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.

Subject Areas

Ionic liquid; synergistic activation; aminoethanol; 2-oxazolidinone; atmospheric CO2; sustainable catalysis

Comments (1)

Comment 1
Received: 19 August 2019
Commenter: Yunong Li
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.
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