Citation: 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]. Chinese Journal of Organic Chemistry, ;2017, 37(11): 2962-2971. doi: 10.6023/cjoc201703015 shu

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

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

Corresponding author: Chen Zhanguo, chzhg@snnu.edu.cn
Received Date: 7 March 2017
Revised Date: 10 May 2017
Available Online: 18 November 2017
Fund Project: 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)the Innovation Foundation of Postgraduate Cultivation of Shaanxi Normal University 2008CXB009the Natural Science Foundation of Shaanxi Province 2009JM2011

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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.
- vicinal bromoamine,
- β, β-dicyanostyrene derivative,
- amide,
- N-bromo-succinimide
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