Synthesis of 3-Hydroxy-3-heterocyclebutylamide Derivatives Using Carbamoylsilanes as an Amide Source

doi:10.6023/cjoc201906033

Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (12): 3560-3566.DOI: 10.6023/cjoc201906033 Previous Articles Next Articles

Special Issue: 元素有机化学合辑2018-2019；有机硅化学虚拟合辑

氨甲酰基硅烷作为氨酰基源合成3-羟基-3-杂环丁基甲酰胺衍生物

张鹏鹏, 陈雯雯, 冯花, 陈建新

山西师范大学化学与材料科学学院山西临汾 041004

收稿日期:2019-06-28 修回日期:2019-07-22 发布日期:2019-08-07
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）和山西省自然科学青年基金（No.201701D221033）资助项目.

Synthesis of 3-Hydroxy-3-heterocyclebutylamide Derivatives Using Carbamoylsilanes as an Amide Source

Zhang Pengpeng, Chen Wenwen, Feng Hua, Chen Jianxin

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

Received:2019-06-28 Revised:2019-07-22 Published:2019-08-07
Supported by:
Project supported by the Foundation for Returness Overseas Scientists of Shanxi Province (No. 0713), the Natural Science Foundation of Shanxi Province (No. 2012011046-9), and the Natural Science Youth Foundation of Shanxi Province (No. 201701D221033).

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Abstract

3-Hydroxy-3-heterocyclebutyl amide derivatives were directly synthesized in 56%~85% yields by nucleophilic addition of various carbamoylsilanes to oxetane-3-one or thietane-3-one in toluene under mild and catalyst-free conditions. This method will provide an efficient route for the synthesis of drugs containing four-membered heterocycles which have not additional stereocentres. The procedure can prepare 3-hydroxy-3-heterocyclebutyl tertiary, secondary and primary amides as well as having a stereocentre connecting with nitrogen atom by selecting different carbamoylsilanes. A comparison of the results obtained from reaction of various carbamoylsilanes indicated that the size of group on the amide group was an important factor in the addition reaction, which influenced on both the reaction time and yields. The reaction has the advantages of mild conditions, less by-products, good yield and simple post-treatment, and is a new method for the efficient preparation of 3-hydroxy-3-heterocycle butylamides.

Key words: carbamoylsilane, α-hydroxyamides, heterocyclicbutylamides, nucleophilic addition, synthetic methods

Cite this article

Zhang Pengpeng, Chen Wenwen, Feng Hua, Chen Jianxin. Synthesis of 3-Hydroxy-3-heterocyclebutylamide Derivatives Using Carbamoylsilanes as an Amide Source[J]. Chinese Journal of Organic Chemistry, 2019, 39(12): 3560-3566.

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氨甲酰基硅烷作为氨酰基源合成3-羟基-3-杂环丁基甲酰胺衍生物

Synthesis of 3-Hydroxy-3-heterocyclebutylamide Derivatives Using Carbamoylsilanes as an Amide Source

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