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2013 , Vol. 33 >Issue 9: 1960 - 1964

DOI: https://doi.org/10.6023/cjoc201302016

研究论文

以汉斯酯1,4-二氢吡啶为还原剂的还原胺化反应研究

  • 黄新炜 ,
  • 刘建利
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  • a 西北大学生命科学学院 西部资源生物与现代生物技术省部共建教育部重点实验室 西安 710069;
    b 西安文理学院化学与化学工程学院 西安 710065

收稿日期: 2013-03-02

  修回日期: 2013-04-26

  网络出版日期: 2013-05-24

基金资助

国家自然科学基金(Nos. 20872118, 30070905);陕西省重点实验室基金(Nos. 2010JS097, 11JS090, 12JS110);陕西省教育厅基金(No. 08jk477)资助项目

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Reductive Amination Reaction Using Hantzsch Ester 1,4-Dihydropyridine as Reducing Reagent

  • Huang Xinwei ,
  • Liu Jianli
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  • a Key Laboratory of Resource Biology and Biotechnology in Western China, Ministry of Education, School of Life Science, Northwest University, Xi'an 710069;
    b School of Chemistry and Chemical Engineering, Xi'an University of Arts and Science, Xi'an 710065

Received date: 2013-03-02

  Revised date: 2013-04-26

  Online published: 2013-05-24

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 20872118, 30070905), the Key Laboratory Fund of Shaanxi Province of China (Nos. 2010JS097, 11JS090, 12JS110) and the Foundation of the Education Department of Shaanxi Province (No. 08jk477)

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摘要

还原胺化是有机合成中的重要反应, 即醛和酮在适当还原剂作用下与伯胺或仲胺制备仲、叔胺. 汉斯酯1,4-二氢吡啶衍生物(HEH)作为仿生有机还原剂已被用于α,β-不饱和羰基化合物、缺电子的共轭烯烃和亚胺的选择性还原以及还原胺化等重要的有机反应中. 以HEH为还原剂, 7-氨基-4-甲基香豆素与常见的醛为模型来探索通过还原胺化反应标记醛类化合物的可行性, 共得到16个还原胺化产物, 其中13个化合物未见文献报道.

关键词： 汉斯酯1,4-二氢吡啶; 还原胺化; 香豆素; 醛; 标记

本文引用格式

黄新炜 , 刘建利 . 以汉斯酯1,4-二氢吡啶为还原剂的还原胺化反应研究[J]. 有机化学, 2013 , 33(9) : 1960 -1964 . DOI: 10.6023/cjoc201302016

Abstract

Reductive amination is an important reaction in organic synthesis. Aldehyde and ketone can react with primary and secondary amine in the presence of appropriate reducing reagent to afford secondary and tertiary amine. Hantzsch ester 1,4-dihydropyridine (HEH) is employed in the selective reduction and reductive amination of α,β-unsaturated carbonyl compounds, electron-deficient conjugate alkene and imine as a biomimetic organic reductant. In this paper, the possibility of labeling aldehyde by reductive amination using HEH as reductant, 7-amino-4-methylcoumarin and aldehydes as models was studied. Sixteen products were synthesized, among them, thirteen compounds were not reported in the literature.

Key words： Hantzsch ester 1,4-dihydropyridine; reductive amination; coumarin; aldehyde; label

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