Synthesis of α-(N-Sulfonyl)amino Amides Derivatives Using Carbamoylsilanes as an Amide Source

doi:10.6023/cjoc201803054

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (8): 1993-2001.DOI: 10.6023/cjoc201803054 Previous Articles Next Articles

Special Issue: 有机硅化学虚拟合辑

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氨甲酰基硅烷作为氨酰基源合成α-磺酰氨基酰胺衍生物

韩宇玲, 仝文婷, 刘慧, 陈建新

山西师范大学化学与材料科学学院临汾 041004

收稿日期:2018-03-30 修回日期:2018-05-13 发布日期:2018-05-24
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）和山西师范大学文理学院基金（No.WL2016CXCY-YJ-30）资助项目.

Synthesis of α-(N-Sulfonyl)amino Amides Derivatives Using Carbamoylsilanes as an Amide Source

Han Yuling, Tong Wenting, Liu Hui, Chen Jianxin

College of Chemistry and Material Science, Shanxi Normal University, Linfen 041004

Received:2018-03-30 Revised:2018-05-13 Published:2018-05-24
Contact: 10.6023/cjoc201803054 E-mail:jjxxcc2002@yahoo.com
Supported by:
Project supported by the Shanxi Provincal Foundation for Returness Overseas Scientists (No. 0713), the Natural Science Foundation of Shanxi Province (No. 2012011046-9), and the Foundation of the Modern College of Arts and Science, Shanxi Normal University (No. WL2016CXCY-YJ-30).

1. Synthesis of α-(N-Sulfonyl)amino Amides Derivatives Using Carbamoylsilanes as an Amide Source.PDF(1139KB)

Abstract

α-(N-Sulfonyl)amino amide derivatives are directly synthesized in 71%~89% yields by the reaction of carbamoylsilanes with various N-sulfonylimines in benzene under catalyst-free conditions. The procedure can prepare both tertiary and secondary α-amino amides. A comparison of the results obtained from the N-sulfonylimines containing the variety of alkyl, aryl and heterocyclic ring indicated that the electronic effect was an important factor in the addition reaction, which influenced on the rate and yields of the reaction. The new method is simple and mild procedure, no catalysts conditions, less byproducts and good yields for the preparation of α-aminoamides.

Key words: carbamoylsilane, α-amino amide, N-sulfonylimine, nucleophilic addition, synthetic method

Cite this article

Han Yuling, Tong Wenting, Liu Hui, Chen Jianxin. Synthesis of α-(N-Sulfonyl)amino Amides Derivatives Using Carbamoylsilanes as an Amide Source[J]. Chin. J. Org. Chem., 2018, 38(8): 1993-2001.

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氨甲酰基硅烷作为氨酰基源合成α-磺酰氨基酰胺衍生物

Synthesis of α-(N-Sulfonyl)amino Amides Derivatives Using Carbamoylsilanes as an Amide Source

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