有机化学 ›› 2022, Vol. 42 ›› Issue (11): 3835-3842.DOI: 10.6023/cjoc202206011 上一篇    下一篇

研究论文

温和条件下苯炔与2-羟基嘧啶加成合成2-芳氧基嘧啶类衍生物

王文鹏, 杨春红, 刘海超, 王喜存*(), 权正军*   

  1. 西北师范大学化学化工学院 兰州 730070
  • 收稿日期:2022-06-08 修回日期:2022-07-12 发布日期:2022-07-13
  • 通讯作者: 王喜存, 权正军
  • 作者简介:
    †共同第一作者
  • 基金资助:
    国家自然科学基金(22067018); 国家自然科学基金(22101232); 甘肃省自然科学基金(20YF3GA023); 甘肃省自然科学基金(20JR5RA210)

Addition of Benzyne to 2-Hydroxypyrimidine to Synthesize 2-Aryloxypyrimidine Derivatives under Mild Conditions

Wenpeng Wang, Chunhong Yang, Haichao Liu, Xicun Wang(), Zhengjun Quan   

  1. College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070
  • Received:2022-06-08 Revised:2022-07-12 Published:2022-07-13
  • Contact: Xicun Wang, Zhengjun Quan
  • About author:
    †These authors contributed equally to this work.
  • Supported by:
    National Natural Science Foundation of China(22067018); National Natural Science Foundation of China(22101232); Natural Science Foundation of Gansu Province(20YF3GA023); Natural Science Foundation of Gansu Province(20JR5RA210)

嘧啶芳基醚衍生物因具有多样的生物活性和药理学特性而受到化学家的广泛关注. 利用2-(三甲基甲硅烷基)苯基三氟甲烷磺酸酯作为苯炔源, 与2-羟基嘧啶发生加成反应, 以中等至良好的产率合成了一系列2-芳氧基嘧啶类衍生物. 与传统的方法相比, 该方法具有无需过渡金属催化, 嘧啶底物易于制备, 底物官能团兼容性强和产物产率高等优点.

关键词: 苯炔, 嘧啶衍生物, 亲核加成, 2-苯氧基嘧啶

Pyrimidine aryl ether derivatives have attracted widespread attention from chemists for their diverse biological activity and pharmacological properties. In this paper, a series of pyrimidine-2-arylether derivatives were synthesized with moderate to good yield by using 2-(trimethylsilyl)phenyl trifluoromethanesulfonate as a source of benzyne to react with 2-hydroxypyrimidine. Compared with the traditional method, this method has the advantages of transition-metal-free, easy preparation of 2-aryloxypyrimidine derivatives, wide functional group compatibility and high yield.

Key words: benzyne, pyrimidine derivatives, nucleophilic addition, 2-phenoxy pyrimidine