Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (11): 2122-2128.DOI: 10.6023/cjoc201205034 Previous Articles     Next Articles

Articles

2-酯基-1,5-苯并氧氮杂(艹卓)的合成及反应副产物的研究

刘倩a, 赵利飞a, 李文红b, 李媛a   

  1. a 河北师范大学化学与材料科学学院 石家庄 050024;
    b 河北工业职业技术学院环境与化学工程系 石家庄 050091
  • 收稿日期:2012-05-29 修回日期:2012-07-11 发布日期:2012-07-17
  • 通讯作者: 李媛 E-mail:liyuanhbsd@163.com
  • 基金资助:

    国家自然科学基金(No. 20972040)资助项目.

Synthesis of 2-Ester-substituted-1,5-benzoxazepines and Studies on the By-product in the Reaction

Liu Qiana, Zhao Lifeia, Li Wenhongb, Li Yuana   

  1. a College of Chemistry and Material Science, Hebei Normal University, Shijiazhuang 050024;
    b Environment and Chemical Engineering, Hebei College of Industry and Technology, Shijiazhuang 050091
  • Received:2012-05-29 Revised:2012-07-11 Published:2012-07-17
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 20972040).

A series of new 1,5-benzoxazepines have been synthesized from substituted benzene, maleic anhydride and 2-aminophenol (4-chloro-2-aminophenol) and identified by IR, 1H NMR, MS (HRMS) techniques and elemental analysis. Meanwhile, the structure of one main by-product 2-benzoylmethyl-2H-1,4-benzoxazin-3(4H)-one (6h') was identified, and the possible mechanism of producing the by-product was proposed. The optimization of reaction conditions showed that the reactions were performed in DMF solvent, at refluxed temperature and catalyzed by p-toluenesulfonic acid, and 2-ester-sub-stituted-1,5-benzoxazepines 6 were the main products. While, the reactions were performed in methyl alcohol, at refluxed temperature and catalyzed by acetic acid, and the by-product 6h' was formed in good yield.

Key words: Michael addition, 1,5-benzoxazepine, 2-aminophenol, 4-chloro-2-aminophenol, reaction mechanism