Selective Reduction of β-Keto Amides to α,β-Unsaturated Olefinic Amides and β-Hydroxy Amides by Using Sodium Borohydride as the Reductant

doi:10.6023/cjoc201603020

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (8): 1890-1894.DOI: 10.6023/cjoc201603020 Previous Articles Next Articles

ARTICLE

硼氢化钠选择性还原乙酰乙酰苯胺至不饱和烯胺和β-羟基酰胺

陈翠, 徐松森, 刘卫兵

广东石油化工学院化学工程学院茂名 525000

收稿日期:2016-03-13 修回日期:2016-03-29 发布日期:2016-04-15
通讯作者: 陈翠 E-mail:cc161002@gdupt.edu.cn
基金资助:
广东省优秀青年基金（No. 2013LYM_0059）资助项目.

Selective Reduction of β-Keto Amides to α,β-Unsaturated Olefinic Amides and β-Hydroxy Amides by Using Sodium Borohydride as the Reductant

Chen Cui, Xu Songsen, Liu Weibing

College of Chemical Engineering, Guangdong University of Petrochemical Technology, Maoming 525000

Received:2016-03-13 Revised:2016-03-29 Published:2016-04-15
Supported by:
Project supported by the Excellent Youth Foundation of Guangdong Province (No. 2013LYM_0059).

1. Selective Reduction of β-Keto Amides to α,β-Unsaturated Olefinic Amides and β-Hydroxy Amides by Using Sodium Borohydride as the Reductant.PDF(3290KB)

Abstract

This paper reports a simple method for the synthesis of α,β-unsaturated olefinic amides from β-keto amides in the presence of NaBH₄ and alkali. However, this reaction only leads to quantitatively reduction product of carbonyl compounds in the presence of NaBH₄ and FeCl₃. The structures of products were confirmed by ¹H NMR and ¹³C NMR spectra. In addition, a possible reaction mechanism was also proposed.

Key words: β-keto amides, α,β-unsaturated olefinic amides, reduction of carbonyl, NaBH₄

Cite this article

Chen Cui, Xu Songsen, Liu Weibing. Selective Reduction of β-Keto Amides to α,β-Unsaturated Olefinic Amides and β-Hydroxy Amides by Using Sodium Borohydride as the Reductant[J]. Chin. J. Org. Chem., 2016, 36(8): 1890-1894.

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硼氢化钠选择性还原乙酰乙酰苯胺至不饱和烯胺和β-羟基酰胺

Selective Reduction of β-Keto Amides to α,β-Unsaturated Olefinic Amides and β-Hydroxy Amides by Using Sodium Borohydride as the Reductant

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