苯基硼酸催化酰胺键构建方法研究

Study on the synthesis of amide compound by arylboronic acid-catalyzation

酰胺键是一种可表现出高生理活性的特殊结构,形成酰胺最理想的途径是羧酸与胺直接反应,但必须要在强热的条件下才可生成。为了解决此问题,研究了一种通过利用简单的芳基硼酸催化,在较为缓和的条件下使脂肪酸与伯胺直接缩合构建酰胺的方法,以苯乙酸与苄胺的直接酰胺化建立反应体系,对反应催化剂种类、催化剂用量、反应溶剂、反应时间以及反应温度进行了优化。结果表明:以氟苯为溶剂,苯硼酸为催化剂,先在回流温度下处理有机酸1h后,再加入脂肪胺继续反应12h,在此最佳反应条件下,可获得对应酰胺的收率在80%以上,采用1 H NMR和13C NMR对所得产物的结构进行了表征。方法操作简单,产物易于纯化,是一种新的制备酰胺类化合物的有效方法。

Amide bond is a special structure that can exhibit high physiological activity.The most ideal way to form amide is the direct reaction between carboxylic acid and amine,but this reaction has to be under strong heat condition.A method is proposed for direct synthesis of amides by direct condensation of fatty acids and primary amines under milder conditions,namely catalyzed by simple arylboronic acids.The reaction system is established by direct amidation of phenylacetic acid and benzylamine.The type,amount of catalyst,reaction solvent,reaction time,and reaction temperature are optimized.The result shows that with fluorobenzene as solvent and phenylboronic acid as catalyst,organic acids are firstly treated for 1 h at reflux temperature,then the reaction continues for 12 h after adding fatty amines,and under the optimum reaction condition,the yield of the corresponding amide is above 80%.The product is characterized by 1H NMR and 13 C NMR.The method is a new simple effective method for preparing amide compounds and the product is easy to purify.