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


张鹏鹏a, 韩生华b, 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
  • 基金资助:

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

Zhang Pengpenga, Han Shenghuab, Chen Jianxina   

  1. 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).

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