State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China.
College of Pharmacy, Nankai University, Tianjin 300353, China.
Molecules. 2018 Nov 20;23(11):3033. doi: 10.3390/molecules23113033.
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.
为了规避由 2-氨基乙醇和 CO₂合成噁唑烷酮时热力学的限制，并在常压下实现 CO₂的掺入，开发了一种质子离子液体促进的炔丙醇、CO₂和 2-氨基乙醇的三组分反应，以生产 2-噁唑烷酮和等摩尔量的α-羟基酮。详细考察了离子液体结构、反应温度和反应时间。发现 15mol% 1,5,7-三氮杂二环[4.4.0]癸-5-烯([TBDH][TFE])三氟乙醇能够协同激活底物和 CO₂，从而在常压 CO₂压力下催化此级联反应。通过采用这种特定任务的离子液体作为可持续催化剂，2-氨基乙醇的不同取代基在 80°C 下反应 12 小时后，以中等至优异的收率转化为 2-噁唑烷酮。
