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

Molecules. 2018 Nov 20;23(11):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% 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.

Keywords: 2-oxazolidinone; aminoethanol; atmospheric CO2; ionic liquid; sustainable catalysis; synergistic activation.

MeSH terms

  • Alkynes / chemistry
  • Carbon Dioxide / chemistry
  • Ethanolamines / chemistry
  • Ionic Liquids / chemistry*
  • Oxazolidinones / chemical synthesis*
  • Oxazolidinones / chemistry
  • Propanols / chemistry
  • Temperature
  • Thermodynamics

Substances

  • Alkynes
  • Ethanolamines
  • Ionic Liquids
  • Oxazolidinones
  • Propanols
  • Carbon Dioxide
  • propargyl alcohol