Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (9): 2191-2196.DOI: 10.6023/cjoc201603032 Previous Articles     Next Articles



陈战国, 侯丹, 刘德娥, 惠文萍   

  1. 陕西师范大学化学化工学院 陕西省大分子科学实验室 西安 710119
  • 收稿日期:2016-03-18 修回日期:2016-04-22 发布日期:2016-05-06
  • 通讯作者: 陈战国
  • 基金资助:


Three-Component Synthesis of 2-Oxazolines from Ethyl α-Cyanocinnamate Derivatives with Amides and N-Bromosuccinimide

Chen Zhanguo, Hou Dan, Liu De'e, Hui Wenping   

  1. Key Laboratory of Macromolecular Science of Shaanxi Province, School of Chemistry and Chemical Engineering, ShaanxiNormal University, Xi'an 710119
  • Received:2016-03-18 Revised:2016-04-22 Published:2016-05-06
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No.20572066), the Natural Science Foundation of Shaanxi Province (No.2009JM2001) and the Innovation Foundation of Postgraduate Cultivation of Shaanxi Normal University (No.2008CXB009).

An easy and efficient new method for the three-component synthesis of 2-oxazolines from ethyl α-cyanocinnamate derivatives with amide and N-bromosuccinimide has been developed. A series of ethyl α-cyanocinnamate derivatives can be smoothly con-verted into corresponding 2-oxazoline derivatives promoted by Na2CO3 in N,N-dimethylformamide (DMF) at room temperature in high yield (up to 94%). The reactions of 11 structurally different substrates with propionamide, acrylamide, isobutyamide and pentanamide were investigated, respectively. The results indicated that the protocol has applicability in a large scope of ethyl α-cyanocinnamate derivatives and amides. A possible mechanism was proposed and it can explain well the full regiospecificity of the reaction. 39 new compounds were achieved via the three-component synthesis reaction and all the products structures were confirmed by their 1H NMR, 13C NMR and HRMS analysis.

Key words: 2-oxazoline, ethyl α-cyanocinnamate, amide, N-bromosuccinimide