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2020 , Vol. 40 >Issue 6: 1737 - 1744

DOI: https://doi.org/10.6023/cjoc202001020

研究简报

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 ,
  • 韩生华 ,
  • 陈建新
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  • 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

  网络出版日期: 2020-03-31

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.

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

  • Zhang Pengpeng ,
  • Han Shenghua ,
  • Chen Jianxin
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  • College of Chemistry and Material Science, Shanxi Normal University, Linfen, Shanxi 041004;
    College of Chemistry and Engineering, Shanxi Datong University, Datong, Shanxi 037009

Received date: 2019-11-14

  Revised date: 2020-03-04

  Online 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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摘要

几种氨甲酰基硅烷与邻位二酮在无催化剂和氧化剂的温和条件下直接发生选择性氨酰化反应，制备了α-硅氧基-β-羰基仲（伯）酰胺衍生物，收率为62%~90%.氨甲酰基硅烷和邻位二酮的结构的空间位阻都影响在两个羰基上的反应选择性.氨基保护基甲氧甲基和苄基容易脱保护基转化成氢原子，得到α-羟基-β-羰基仲（伯）酰胺衍生物.通过选择不同氨甲酰基硅烷进行反应发现，此方法是选择性合成α-羟基-β-羰基叔酰胺、仲酰胺和伯酰胺衍生物的简易方法.该反应具有条件温和、副产物少、选择性強、产物得率高和后处理简单等优点，是有效合成α-羟基-β-羰基酰胺衍生物的新方法.

关键词： 氨甲酰基硅烷; β-羰基-α-羟基酰胺; 氨酰化; 亲核加成; 邻位二酮

本文引用格式

张鹏鹏 , 韩生华 , 陈建新 . 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[J]. 有机化学, 2020 , 40(6) : 1737 -1744 . DOI: 10.6023/cjoc202001020

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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