Chinese Journal of Organic Chemistry >
Synthesis of Vicinal Bromoamine Compounds via Three Components Reaction of β,β-Dicyanostyrene/Amide/N-Bromo-succinimide
Received date: 2017-03-07
Revised date: 2017-05-10
Online published: 2017-07-18
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).
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.
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
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