Synthesis of α-Hydroxyamides from a Carbamoylsilane and Aldehydes

doi:10.6023/cjoc201408006

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (1): 223-227.DOI: 10.6023/cjoc201408006 Previous Articles Next Articles

Notes

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

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 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 Yuan^a,b, Li Weidong^a, Tong Wenting^a, Chen Jianxin^a

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 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).

1. Synthesis of α-Hydroxyamides from a Carbamoylsilane and Aldehydes.PDF(1866KB)

Abstract

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

Cite this article

Yao Yuan, Li Weidong, Tong Wenting, Chen Jianxin. Synthesis of α-Hydroxyamides from a Carbamoylsilane and Aldehydes[J]. Chin. J. Org. Chem., 2015, 35(1): 223-227.

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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

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