有机化学 ›› 2017, Vol. 37 ›› Issue (8): 2078-2085.DOI: 10.6023/cjoc201702015 上一篇    下一篇

研究论文

2-巯基嘧啶与碳酸Morita-Baylis-Hillman酯的选择性S-烯丙基烷基化

杨靖亚a, 李娜娜a, 周红艳b, 李天媛a, 谢栋泰a, 李政a   

  1. a 西北师范大学化学化工学院 兰州 730070;
    b 甘肃农业大学理学院 兰州 730070
  • 收稿日期:2017-02-14 修回日期:2017-03-24 出版日期:2017-08-25 发布日期:2017-04-13
  • 通讯作者: 杨靖亚 E-mail:yangjy@nwnu.edu.cn
  • 基金资助:

    国家自然科学基金(Nos.21362034,21462038)和高等学校博士学科点专项科研基金(No.20136203120005)资助项目.

Selective S-Allylic Alkylation of 2-Thiopyrimidine with Morita-Baylis-Hillman Carbonates

Yang Jingyaa, Li Nanaa, Zhou Hongyanb, Li Tianyuana, Xie Dongtaia, Li Zhenga   

  1. a College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070;
    b College of Science, Gansu Agricultural University, Lanzhou 730070
  • Received:2017-02-14 Revised:2017-03-24 Online:2017-08-25 Published:2017-04-13
  • Contact: 10.6023/cjoc201702015 E-mail:yangjy@nwnu.edu.cn
  • Supported by:

    Project supported by the National Nature Science Foundation of China (Nos. 21362034, 21462038) and the Research Fund for the Doctoral Program of Higher Education of China (No. 20136203120005).

发展了一种1,4-二氮杂二环[2.2.2]辛烷(DABCO)催化2-巯基嘧啶与碳酸Morita-Baylis-Hillman (MBH)酯的S-烯丙基烷基化反应新方法.一系列碳酸MBH酯与2-巯基嘧啶反应并以55%~99%的产率得到S-烯丙基烷基化产物.具有专一的化学选择性和良好的区域选择性,反应条件温和,反应时间短,底物适用广泛,有良好的应用前景.

关键词: S-烯丙基烷基化, 2-巯基嘧啶, 碳酸MBH酯, 烯丙基化合物, 化学选择性, 区域选择性, 杂环化合物

The S-allylic alkylation of 2-thiopyrimidine with Morita-Baylis-Hillman (MBH) carbonates catalyzed by 1,4-diazabicyclo[2.2.2]octane (DABCO) has been developed. A variety of Morita-Baylis-Hillman (MBH) carbonates reacted with 2-thiopyrimidine and gave the desired S-allylic alkylated products in 55%~99% yields with exclusive chemoselectivity and excellent regioselectivity. The mild reaction conditions, short reaction time, and broad substrate scope make this method very practical.

Key words: S-allylic alkylation, 2-thiopyrimidine, Morita-Baylis-Hillman (MBH) carbonates, allylic compounds, chemoselectivity, regioselectivity, heterocycles