氨甲酰基硅烷与醛反应直接合成α-羟基酰胺

Synthesis of α-Hydroxyamides from a Carbamoylsilane and Aldehydes

N,N-二甲基氨甲酰基三甲基硅烷与一系列醛反应直接合成了α-羟基酰胺衍生物,收率多数为71%~91%,其结构用元素分析、1^H NMR、13^C NMR和IR等方法进行了表征.通过研究反应的影响因素发现,醛基相连基团的电子效应是影响反应的重要因素,它既影响反应完成的时间,又影响分离产物的产率.提出了可能的反应机理.该反应具有条件温和、副产物少、产物得率高和后处理简单等优点,是一种有效合成α-羟基酰胺的新方法.

a-Hydroxyamides are directly synthesized by the reaction ofN, N-dimethylcarbamoyl（trimethyl）silane with various aldehydes. Most of yields are 71%~91%. Their structures were confirmed by 1^H NMR, 13^C NMR, IR and elemental analysis. Through carbamoylsilane reacted with the variety of aldehydes, the results indicated that the electronic effect was an important factor in the addition reaction, which influenced on the rate and yields of the reaction. A reaction mechanism is proposed. The main advantages of the developed methodology are mild reaction conditions, less byproducts, high yields of products and simple work-up procedure. An effective synthesis method of a-hydroxyamides has been developed.