Synthesis of Vicinal Bromoamine Compounds via Three Components Reaction of β,β-Dicyanostyrene/Amide/N-Bromo-succinimide

doi:10.6023/cjoc201703015

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (11): 2962-2971.DOI: 10.6023/cjoc201703015 Previous Articles Next Articles

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β,β-二氰基苯乙烯/酰胺/N-溴代丁二酰亚胺三组分合成相应的邻溴代胺

康梦, 惠文萍, 侯丹, 陈战国

应用表面与胶体化学教育部重点实验室陕西省大分子科学重点实验室陕西师范大学化学化工学院西安 710119

收稿日期:2017-03-07 修回日期:2017-05-10 发布日期:2017-07-18
通讯作者: 陈战国 E-mail:chzhg@snnu.edu.cn
基金资助:
陕西省自然科学基金（No.2009JM2011）和陕西师范大学研究生创新基金（No.2008CXB009）资助项目.

Synthesis of Vicinal Bromoamine Compounds via Three Components Reaction of β,β-Dicyanostyrene/Amide/N-Bromo-succinimide

Kang Meng, Hui Wenping, Hou Dan, Chen Zhanguo

Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, Key Laboratory for Macromolecular Science of Shaanxi Province, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710119

Received:2017-03-07 Revised:2017-05-10 Published:2017-07-18
Contact: 10.6023/cjoc201703015 E-mail:chzhg@snnu.edu.cn
Supported by:
Project supported by the Natural Science Foundation of Shaanxi Province (No. 2009JM2011) and the Innovation Foundation of Postgraduate Cultivation of Shaanxi Normal University (No. 2008CXB009).

1. Synthesis of Vicinal Bromoamine Compounds via Three Components Reaction of β,β-Dicyanostyrene/Amide/N-Bromo-succinimide.PDF(1481KB)

Abstract

Vicinal bromoamine derivative belongs to an important class of difunctionalization compounds. New synthetic method and new vicinal bromoamine derivatives are eagerly desired. Thus, a new one-pot protocol for the synthesis of vicinal bromoamines from β,β-dicyanostyrene derivatives/amides/N-bromo-succinimide was developed. In the presence of anhydrous K₂CO₃, β,β-dicyanostyrenes reacted smoothly with amides and N-bromo-succinimide (NBS) to generate the vicinal bromoamine compounds in good to excellent yield (up to 93% yield) at room temperature without the protection of inert gas in CH₂Cl₂. 13 different structural β,β-dicyanostyrene derivatives reacted with 7 different structural amides (acrylamide, acetamide, valeramide, isobutyramide, benzamide, 4-nitrobenzamide, ethylurethanm) and NBS have been investigated in this work. The results indicated that the method is not only widely subjected to β,β-dicyanostyrene, but also suitable for the different type of amide. The structures of all the products were confirmed by their nuclear magnetic resonance spectroscopy (NMR), infrared spectra (IR) and high reso-lution mass spectrometry (HRMS), and the possible reaction mechanism was proposed.

Key words: vicinal bromoamine, β,β-dicyanostyrene derivative, amide, N-bromo-succinimide

Cite this article

Kang Meng, Hui Wenping, Hou Dan, Chen Zhanguo. Synthesis of Vicinal Bromoamine Compounds via Three Components Reaction of β,β-Dicyanostyrene/Amide/N-Bromo-succinimide[J]. Chin. J. Org. Chem., 2017, 37(11): 2962-2971.

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β,β-二氰基苯乙烯/酰胺/N-溴代丁二酰亚胺三组分合成相应的邻溴代胺

Synthesis of Vicinal Bromoamine Compounds via Three Components Reaction of β,β-Dicyanostyrene/Amide/N-Bromo-succinimide

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