羧酸酯与氨甲酰基硅烷反应合成α-羰基酰胺的新方法  

Novel Method for Synthesis of α-Ketoamides from Carboxylic Ester and Carbamoylsilane

作　　者：马江雯 李伟东[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041000

出　　处：《山西师范大学学报（自然科学版）》2016年第4期65-68,共4页Journal of Shanxi Normal University(Natural Science Edition)

基　　金：山西省自然科学基金项目(2012011046-9);山西师范大学大学生创新创业训练项目(SD2014CXXM-53)

摘　　要：α-羰基酰胺在生物学、药物化学和化学合成中是一类重要的化合物,他们的合成方法被广泛的研究.本文报道一种新的合成方法,用N,N-二甲基氨甲酰基三甲基硅烷与一系列羧酸酯在无水无氧、110℃和甲苯作溶剂的条件下反应,合成α-羰基酰胺衍生物.反应生成的α-羰基酰胺的结构用元素分析、1H NMR和13C NMR等方法进行了表征.通过研究反应的影响因素发现,反应底物羧酸酯中,与羰基相连的芳基的电子效应是该反应的重要影响因素,芳基的吸电子能力越強,反应越快,产率越高.该方法反应温和,操作简单,原料稳定,不使用催化剂,可操作性较强,具有重要的合成应用价值.α-Ketoamides are a very important class of organic compounds in biology,pharmaceutical chemistry and chemical synthesis,whose synthesis have been investigated extensively. Here,we report a novel synthetic method by N,N-dimethylcarbamoyl（ trimethyl） silane reacted with a series of carboxylic ester in toluene under anhydrous condition at 110 ℃ leading to formation of α-ketoamides derivatires. The structures of the α-ketoamides were characterized by element analysis,1H NMR and13 C NMR spectra.The experimental results showed that the electronic property of aryl group in carboxylic ester is an important factor. The stronger electron-withdrawing ability of the aryl group in carboxylic ester,the faster the process,the higher the yield was obtained. The mild and simple procedure,the stable of carboxylic ester,free catalyst and simple operation provides a valuable method for the preparation of various α-ketoamides.

关 键 词：氨甲酰基硅烷 羧酸酯 羰基酰胺 合成方法 

分 类 号：O621.3[理学—有机化学]