α-羟基-α-氨甲酰基酰胺类化合物的合成新方法  

Novel Synthesis of α-Hydroxy-α-carbamoyl Amide Compounds

作　　者：陈晓娟[1] 张文俊[1] 陈建新[1] 

机构地区：[1]山西师范大学化学与材料科学学院,山西临汾041004

出　　处：《应用化学》2015年第5期547-551,共5页Chinese Journal of Applied Chemistry

基　　金：山西省留学回国人员基金(0713);山西省自然科学基金(2012011046-9);山西师范大学基金(SD2014CXXM-53)资助项目~~

摘　　要：N,N-二甲氨酰基三甲基硅烷与一系列α-羰基酰胺在无水无氧、105℃的条件下反应,较高产率地合成了α-羟基-α-氨甲酰基酰胺类化合物或α-三甲基硅氧基-α-氨甲酰基酰胺衍生物。其结构用元素分析、1HNMR、13CNMR和IR等技术手段进行了表征。通过研究反应机理和影响反应的因素发现,在α-羰基上连的烃基的空间位阻是该加成反应的重要影响因素,而电子效应则影响反应的速率。提出了可能的反应机理。α-Hydroxy-α-carbamoylamides are important synthetic intermediates and also serve as valuable agents in medicinal chemistry. Herein, a novel method for synthesis of α-hydroxy-α-carbamoylamides was developed and the reaction mechanism involving two intermediates was proposed. Good yields of α-hydroxy-α- carbamoylamides or α-trimethylsiloxy-α-carbamoylamides are obtained by the addition of N, N- dimethylcarbamoyl（trimethyl） silane to a series of α-ketoamides under anhydrous condition at 105 ℃. Their structures were characterized by elemental analysis, 1^H NMR, 13^C NMR and IR spectra. The sterie hindrance is found to be an important factor in the addition reaction and the electronic effect can influence the rate of the reaction.

关 键 词：氨甲酰基硅烷 α-羰基酰胺 α-羟基-α-氨甲酰基酰胺 加成反应 

分 类 号：O621.3[理学—有机化学]