Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (6): 1260-1269.DOI: 10.6023/cjoc201412032 Previous Articles     Next Articles



吕强a,b, 芦昕婷b, 戴明b, 刘世梦b, 朱为宏a, 杜葩c, 吕龙b   

  1. a 华东理工大学化学与分子工程学院 上海 200237;
    b 中国科学院上海有机化学研究所 有机氟化学重点实验室 上海 200032;
    c 上海应用技术学院化学与环境工程学院 上海 201418
  • 收稿日期:2015-12-18 修回日期:2015-02-17 发布日期:2015-02-18
  • 通讯作者: 杜葩
  • 基金资助:

    "十二五"国家科技支撑计划(No. 2011BAE06B02)资助项目.

Synthesis and Bioactivity of 2-Benzoyl Pyrimidine Derivatives

Lü Qianga,b, Lu Xintingb, Dai Mingb, Liu Shimengb, Zhu Weihonga, Du Pac, Lü Longb   

  1. a School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai 200237;
    b Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, Shanghai 200032;
    c School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418
  • Received:2015-12-18 Revised:2015-02-17 Published:2015-02-18
  • Supported by:

    Project supported by the National Key Technologies R&D Program (No. 2011BAE06B02).

2-Benzoyl pyrimidine as a secondary leading structure is developed by twice optimization of 2-pyrimidinoxy-N- aryl benzylamine. Based on this structure, thirty six 2-benzoyl pyrimidine derivatives have been designed and synthesized. All compounds are determined by 1H NMR, 13C NMR and HRMS. Their interior fungicidal activities show that R1 substituent prefers phenyl or heterocyclic group with 2-halo or 2-alkyl group. When introducing fluoride to 6-position on benzene ring, the fungicidal activity is maintained at a similar level. 4,6-Dimethoxy group on pyrimidine ring was recognized as a best substituent by far. The activity is seriously decreased when methyl group is fixed on 5-position of pyrimidine. Even the fungicidal activities become completely disappeared when the ketone group is reduced to hydroxyl group. Among them, three compounds 2,3-dichloro-N-(2-(4,6-dimethoxypyrimidine-2-carbonyl)phenoxy)-N-methylbenzamide (4AHl), 2,5-dichloro-N-(2-(4,6-dime- thoxypyrimidine-2-carbonyl)phenoxy)-N-methylbenzamide (4AHn) and N-(2-(4,6-dimethoxypyrimidine-2-carbonyl)-3-fluoro- phenoxy)-N,2-dimethylbenzamide (4AFd) exhibit comparable fungicidal activity against cucumber powdery mildew to the reference metrafenone.

Key words: 2-benzoyl pyrimidine, synthesis, structral optimization, biological activity