Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (7): 1680-1686.DOI: 10.6023/cjoc201801016 Previous Articles     Next Articles



徐姣a,b, 马玲a, 刘秀波b, 马伟a,b, 马岩c, 王道林d   

  1. a 东北林业大学 林木遗传育种国家重点实验室 哈尔滨 150040;
    b 黑龙江中医药大学药学院 哈尔滨 150040;
    c 哈尔滨商业大学工商管理学院 哈尔滨 150040;
    d 渤海大学化学化工学院 锦州 121003
  • 收稿日期:2018-01-08 修回日期:2018-03-25 发布日期:2018-04-12
  • 通讯作者: 马伟, 王道林;
  • 基金资助:


Synthesis and Fungicidal Activity of Novel Benzothiophene-Fused Pyrido[1,2-a]pyrimidine Derivatives

Xu Jiaoa,b, Ma Linga, Liu Xiubob, Ma Weia,b, Ma Yanc, Wang Daolind   

  1. a State Key Laboratory of Tree Genetics and Breeding, Northeast Forestry University, Harbin 150040;
    b College of Pharmacy, Heilongjiang University of Chinese Medicine, Harbin 150040;
    c School of business administration, Harbin University of Commerce, Harbin 150040;
    d College of Chemistry and Chemical Engineering, Bohai University, Jinzhou 121003
  • Received:2018-01-08 Revised:2018-03-25 Published:2018-04-12
  • Contact: 10.6023/cjoc201801016;
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 31770688), the National Public Welfare Industry Special (No. 201404718), the Harbin Research and Development Fund of Applied Technology (No. 2017RAQXJ129) and the Scientific Research Fund of the Health Planning Committee of Heilongjiang (No. 2017-579).

A series of novel benzothieno[3',2':2,3]pyrido[4,5-d]pyrido[1,2-a]pyrimidines are prepared via Pictet-Spengler reaction of 2-(3-aminobenzothiophene-2-yl)-4H-pyrido[1,2-a]pyrimidin-4-one using sulfamic acid as a catalyst, which in turn were obtained from the Thorpe-Ziegler isomerization of 2-(chloromethyl)-4H-pyrido[1,2-a]pyrimidin-4-one with 2-mercapto-benzonitrile. The structures of the products were characterized by FT-IR, 1H NMR, 13C NMR spectra and elemental analysis. The fungicidal activities of the prepared compounds were also preliminarily evaluated. For example, 5b exhibited more than 96% inhibition rate to Botrytis cinerea and Gibberella zeae at 50 mg/L, 5f exhibited 98% inhibition rate to Sclerotonia sclerotiorum at 50 mg/L, and 5g, 5i exhibited more than 93% inhibition rate to Alternaria alternata at 50 mg/L.

Key words: pyrido[1,2-a]pyrimidine, benzothiophene, 2-mercaptobenzonitrile, Pictet-Spengler reaction, synthesis, fungicidal activity