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2017 , Vol. 37 >Issue 8: 2078 - 2085

DOI: https://doi.org/10.6023/cjoc201702015

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 ,
  • 李娜娜 ,
  • 周红艳 ,
  • 李天媛 ,
  • 谢栋泰 ,
  • 李政
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  • 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

  网络出版日期: 2017-04-13

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.

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

  • Yang Jingya ,
  • Li Nana ,
  • Zhou Hongyan ,
  • Li Tianyuan ,
  • Xie Dongtai ,
  • Li Zheng
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  • a College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070;
    b College of Science, Gansu Agricultural University, Lanzhou 730070

Received date: 2017-02-14

  Revised date: 2017-03-24

  Online published: 2017-04-13

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).

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摘要

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

本文引用格式

杨靖亚 , 李娜娜 , 周红艳 , 李天媛 , 谢栋泰 , 李政 . 2-巯基嘧啶与碳酸Morita-Baylis-Hillman酯的选择性S-烯丙基烷基化[J]. 有机化学, 2017 , 37(8) : 2078 -2085 . DOI: 10.6023/cjoc201702015

Abstract

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

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