有机化学 ›› 2015, Vol. 35 ›› Issue (1): 223-227.DOI: 10.6023/cjoc201408006 上一篇    下一篇

研究简报

氨甲酰基硅烷与醛反应直接合成α-羟基酰胺

姚远a,b, 李伟东a, 仝文婷a, 陈建新a   

  1. a 山西师范大学化学与材料科学学院 临汾 041004;
    b 山西省临汾市实验中学 临汾 041000
  • 收稿日期:2014-06-23 修回日期:2014-09-10 出版日期:2015-01-25 发布日期:2014-09-25
  • 通讯作者: 陈建新 E-mail:jjxxcc2002@yahoo.com
  • 基金资助:

    山西省留学回国人员基金(No. 0713)、山西省自然科学基金(No. 2012011046-9)、山西师范大学基金(No. SD2014CXXM-53)资助项目.

Synthesis of α-Hydroxyamides from a Carbamoylsilane and Aldehydes

Yao Yuana,b, Li Weidonga, Tong Wentinga, Chen Jianxina   

  1. a College of Chemistry and Material Science, Shanxi Normal University, Linfen 041004;
    b The First Experimental Middle School of Linfen City, Linfen 041000
  • Received:2014-06-23 Revised:2014-09-10 Online:2015-01-25 Published:2014-09-25
  • Supported by:

    Project supported by the Shanxi Province Foundation for Returness Overseas Scientists of China (No. 0713), the Natural Science Foundation of Shanxi Province (No. 2012011046-9), and the Foundation of Shanxi Normal University (No. SD2014CXXM-53).

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、1H NMR、13C 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.

关键词: 亲核加成, 氨甲酰基硅烷, α-羟基酰胺, 醛, 卡宾

α-Hydroxyamides are directly synthesized by the reaction of N,N-dimethylcarbamoyl(trimethyl)silane with various aldehydes. Most of yields are 71%~91%. Their structures were confirmed by 1H NMR, 13C 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 α-hydroxyamides has been developed.

Key words: nucleophilic addition, carbamoylsilane, α-hydroxyamides, aldehydes, carbenes