Efficient Synthesis of β-Keto-α-hydroxy Secondary (Primary) Amides by Selective Aminocarbonylation of Vicinal Diketones Using Carbamoylsilane as an Amide Source

doi:10.6023/cjoc202001020

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (6): 1737-1744.DOI: 10.6023/cjoc202001020 Previous Articles Next Articles

Special Issue: 有机硅化学虚拟合辑

氨甲酰基硅烷作氨酰基源与邻位二酮选择性氨酰化反应合成α-羟基-β-羰基仲(伯)酰胺衍生物

张鹏鹏^a, 韩生华^b, 陈建新^a

a 山西师范大学化学与材料科学学院临汾 041004;
b 山西大同大学化学与工程学院大同 037009

收稿日期:2019-11-14 修回日期:2020-03-04 发布日期:2020-03-31
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）资助项目.

Efficient Synthesis of β-Keto-α-hydroxy Secondary (Primary) Amides by Selective Aminocarbonylation of Vicinal Diketones Using Carbamoylsilane as an Amide Source

Zhang Pengpeng^a, Han Shenghua^b, Chen Jianxin^a

College of Chemistry and Material Science, Shanxi Normal University, Linfen, Shanxi 041004;
College of Chemistry and Engineering, Shanxi Datong University, Datong, Shanxi 037009

Received:2019-11-14 Revised:2020-03-04 Published:2020-03-31
Supported by:
Project supported by the Shanxi Provincal Foundation for Returnees Overseas Scientists (No. 0713), and the Natural Science Foundation of Shanxi Province (No. 2012011046-9).

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Abstract

The selective aminocarbonylation of vicinal diketones using carbamoylsilane as an amide source affords β-keto-α-siloxyamide derivatives in 62%~90% yields under mild conditions without using any oxidants and catalysts. The steric hindrance, which is both from the groups of vicinal diketones and the carbamoylsilanes, affects reaction selectivity on two carbonyl groups. The methoxymethyl or benzyl used as an amino protecting group, can be easily converted into hydrogen atom leading to β-keto-α-hydroxy secondary or primary amides. The simple procedure allows the preparation of various β-keto-α-hydroxy amide derivatives including primary, secondary and tertiary β-keto-α-hydroxy amide derivatives. The reaction has the advantages of mild conditions, less by-products, high selectivity, good yield and simple post-treatment, and it is a new method for the efficient preparation of β-keto-α-hydroxyamides.

Key words: carbamoylsilanes, β-keto-α-hydroxyamides, aminocarbonylation, nucleophilic addition, vicinal diketones

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Zhang Pengpeng, Han Shenghua, Chen Jianxin. Efficient Synthesis of β-Keto-α-hydroxy Secondary (Primary) Amides by Selective Aminocarbonylation of Vicinal Diketones Using Carbamoylsilane as an Amide Source[J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1737-1744.

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氨甲酰基硅烷作氨酰基源与邻位二酮选择性氨酰化反应合成α-羟基-β-羰基仲(伯)酰胺衍生物

Efficient Synthesis of β-Keto-α-hydroxy Secondary (Primary) Amides by Selective Aminocarbonylation of Vicinal Diketones Using Carbamoylsilane as an Amide Source

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