An Efficient Access to α-Dibromosubstituted Arylamides from β-Keto Arylamides

doi:10.6023/cjoc201410008

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (2): 450-454.DOI: 10.6023/cjoc201410008 Previous Articles Next Articles

Notes

乙酰乙酰苯胺类化合物导向的2,2-二溴乙酰苯胺衍生物的合成

刘卫兵, 陈翠, 邱会华

广东石油化工学院化学工程学院茂名 525000

收稿日期:2014-10-08 修回日期:2014-11-11 发布日期:2014-11-11
通讯作者: 刘卫兵 E-mail:lwb409@aliyun.com
基金资助:
广东省自然科学基金(No. S2012040007868)和广东省优秀青年基金(No. 2013LYM_0059)资助项目.

An Efficient Access to α-Dibromosubstituted Arylamides from β-Keto Arylamides

Liu Weibing, Chen Cui, Qiu Huihua

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

Received:2014-10-08 Revised:2014-11-11 Published:2014-11-11
Supported by:
Project supported by the Natural Science Foundation of Guangdong Province (No. S2012040007868) and the Excellent Young Scientist Fund of Education Department of Guangdong Province (No. 2013LYM_0059).

1. An Efficient Access to α-Dibromosubstituted Arylamides from β-Keto Arylamides.PDF(1784KB)

Abstract

A remarkably simple, mild and efficient approach for carbon-carbon bond cleavage of β-keto amides using N-bromobutanimide (NBS) as the bromine source and acetic acid as the catalyst to construct α-dibromosubstituted arylamides is achieved. Moreover, tandem carbon-bromine bond formation, followed by protonation of carbonyl and cleavage of C—C bond in one pot has also been demonstrated. All the reactions were carried out under extremely mild conditions and provided almost quantitative yields of the products.

Key words: carbon-bromine bond formation, carbon-carbon bond cleavage, α-dibromosubstituted arylamides, acetoacetanilides

Cite this article

Liu Weibing, Chen Cui, Qiu Huihua. An Efficient Access to α-Dibromosubstituted Arylamides from β-Keto Arylamides[J]. Chin. J. Org. Chem., 2015, 35(2): 450-454.

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乙酰乙酰苯胺类化合物导向的2,2-二溴乙酰苯胺衍生物的合成

An Efficient Access to α-Dibromosubstituted Arylamides from β-Keto Arylamides

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