Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (3): 590-595.DOI: 10.6023/cjoc201508019 Previous Articles     Next Articles



唐子龙a,b, 夏赞稳a, 李新兴a   

  1. a 湖南科技大学 理论有机化学与功能分子教育部重点实验室 湘潭 411201;
    b 湖南科技大学化学化工学院 湘潭 411201
  • 收稿日期:2015-08-19 修回日期:2015-10-30 发布日期:2015-11-16
  • 通讯作者: 唐子龙
  • 基金资助:

    国家自然科学基金(Nos. 21042011, 21372070)、国家科技计划支撑子项目(No. 2011BAE06B01)和湖南省高校创新平台开放基金(No. 13k089)资助项目.

Stereoselective Synthesis, Crystal Structure and Fungicidal Activity of trans-2,3,6(8)-Trisubstituted-1,3-benzoxazines

Tang Zilonga,b, Xia Zanwena, Li Xinxinga   

  1. a Key Laboratory of Theoretical Organic Chemistry and Functional Molecule, Ministry of Education, Hunan University of Science and Technology, Xiangtan 411201;
    b School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201
  • Received:2015-08-19 Revised:2015-10-30 Published:2015-11-16
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21042011, 21372070), the Sub-project of National Science and Technology Supporting Program of China (Nos. 2011BAE06B01) and the Scientific Research Fund of Hunan Provincial Education Department (No. 13K089).

A series of novel trans-2,3,6(8)-trisubstituted-1,3-benzoxazines were prepared in yields of 38%~80% by reactions of 2-arylaminomethyl phenols with various substituted benzaldehydes in the presence of TMSCl. The reaction showed high trans selectivity. The structures of all the target products were characterized by 1H NMR, 13C NMR, IR and elemental analysis. The fungicidal activities of the prepared compounds were investigated, most of which showed moderate to good activity, compounds 5d and 5f showed growth inhibition of 78.6% against M. oryzae at 50 mg/mL.

Key words: 2,3,6(8)-trisubstituted-1,3-benzoxazine, synthesis, stereoselectivity, fungicidal activity