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
收稿日期: 2016-03-13
修回日期: 2016-03-29
网络出版日期: 2016-04-15
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
Received date: 2016-03-13
Revised date: 2016-03-29
Online published: 2016-04-15
Supported by
Project supported by the Excellent Youth Foundation of Guangdong Province (No. 2013LYM_0059).
以乙酰乙酰苯胺类化合物为原料，在硼氢化钠与碱存在的条件下，通过对羰基的直接还原并进一步脱水，成功地构建出了α，β-不饱和烯酰胺类衍生物；而在硼氢化钠与三氯化铁的条件下，羰基只能还原成羟基，并且以极高的收率得到相应还原产物，其结构经1H NMR和13C NMR得到了确认，并提出了可能的反应机理.
关键词： 乙酰乙酰苯胺; α,β-不饱和烯酰胺类衍生物; 羰基还原; 硼氢化钠
陈翠 , 徐松森 , 刘卫兵 . 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[J]. 有机化学, 2016 , 36(8) : 1890 -1894 . DOI: 10.6023/cjoc201603020
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.
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