Chemical Research in Chinese Universities ›› 2015, Vol. 31 ›› Issue (1): 65-70.doi: 10.1007/s40242-015-4341-x

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Aminobromination of Ethyl α-Cyanocinnamate Derivatives with 1,3-Dibromo-5,5-dimethylhydantoin(DBDMH) as Nitrogen and Halogen Sources

CHEN Zhanguo, LIU Yali, HU Junli, LIU De'e   

  1. Key Laboratory for Macromolecular Science of Shaanxi Province, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710119, P. R. China
  • Received:2014-09-15 Revised:2014-10-08 Online:2015-02-01 Published:2014-11-03
  • Contact: CHEN Zhanguo, E-mail:chzhg@snnu.edu.cn E-mail:chzhg@snnu.edu.cn
  • Supported by:

    Supported by the Natural Science Foundation of Shaanxi Province, China(No.2009JM2001), the Innovation Foundation of Pastgraduate Cultivation of Shaanxi Normal University, China(No.2008CXB009) and the Fundamental Research Funds for the Central Universities of China(No.GK261001095).

Abstract:

1,3-Dibromo-5,5-dimethylhydantoin(DBDMH) was found to be a new and efficient nitrogen/halogen source for the aminobromination of ethyl α-cyanocinnamate derivatives catalyzed by K3PO4. The reaction afforded the aminobrominated products in high yields at room temperature, and the full regiospecificity of all the products were achieved. A possible pathway involving a Michael addition for this aminobromination was suggested.

Key words: Aminobromination, Ethyl α-cyanocinnamate derivative, 1,3-Dibromo-5,5-dimethylhydantoin(DBDMH)