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

ABSTRACT: To circumvent the thermodynamic limitation of the synthesis of oxazolidinones starting from 2-aminoethanols and CO? and realize incorporation CO? under atmospheric pressure, a protic ionic liquid-facilitated three-component reaction of propargyl alcohols, CO? and 2-aminoethanols was developed to produce 2-oxazolidinones along with equal amount of ?-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?, thus catalyzing this cascade reaction under atmospheric CO? 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.

SUBMITTER: Xia S 

PROVIDER: S-EPMC6280151 | biostudies-literature | 2018 Nov

REPOSITORIES: biostudies-literature