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2021 , Vol. 41 >Issue 7: 2831 - 2838

DOI: https://doi.org/10.6023/cjoc202102026

研究论文

N,N-二甲基甲酰胺(DMF)促进羟基氮杂环与卤代烃的专一性N-烷基化反应: 直接高效的吡啶酮类化合物合成方法

  • 韩峰 ,
  • 王婷 ,
  • 冯斌 ,
  • 徐清
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  • a 温州大学化学与材料工程学院 浙江温州 325035
    b 扬州大学化学化工学院 江苏扬州 225002

收稿日期: 2021-02-12

  修回日期: 2021-03-16

  网络出版日期: 2021-04-06

基金资助

国家自然科学基金(21672163); 浙江省自然科学杰出青年基金(LR14B020002)

收起

N,N-Dimethylformamide (DMF)-Promoted SpecificN-Alkylation of Hydroxyl N-Heterocycles with Organohalides: A Direct and Efficient Method for Synthesis of Pyridone Derivatives

  • Feng Han ,
  • Ting Wang ,
  • Bin Feng ,
  • Qing Xu
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  • a College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, Zhejiang 325035
    b School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002
* Corresponding author. E-mail:

Received date: 2021-02-12

  Revised date: 2021-03-16

  Online published: 2021-04-06

Supported by

National Natural Science Foundation of China(21672163); Natural Science Foundation of Zhejiang Province for Distinguished Young Scholars(LR14B020002)

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摘要

在羟基氮杂环化合物与卤代烃的无碱、专一性N-烷基化合成吡啶酮类化合物的反应中,N,N-二甲基甲酰胺(DMF)比其他溶剂具有更好的溶剂效应, 使得该反应可以在更温和条件下得到更高的收率, 而且底物适用范围广. 据机理研究和文献报道, 除了一般的溶剂效应外, DMF还通过在反应中分解出二甲基胺作为碱促进反应进行.

关键词： 羟基氮杂环; 卤代烃; 吡啶酮; N-烷基化; N,N-二甲基甲酰胺(DMF); 溶剂效应

本文引用格式

韩峰 , 王婷 , 冯斌 , 徐清 . N,N-二甲基甲酰胺(DMF)促进羟基氮杂环与卤代烃的专一性N-烷基化反应: 直接高效的吡啶酮类化合物合成方法[J]. 有机化学, 2021 , 41(7) : 2831 -2838 . DOI: 10.6023/cjoc202102026

Abstract

In base-free specificN-alkylation of hydroxylN-heterocycles with organohalides producing pyridone-type products,N,N-dimethylformamide (DMF) was found to be the best solvent for having the most prominent solvent effect among the usual solvents. This not only led to milder reaction conditions and higher yields of the products, but also could broaden the substrate scope of the reaction. Mechanistic studies and the literature revealed that, in addition to the usual solvent effect, DMF can decompose to produce dimethylamine during the reaction, which then works as a base to promote the reaction.

Key words： hydroxylN-heterocycle; organohalide; pyridone; N-alkylation; N,N-dimethylformamide (DMF); solvent effect

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