有机化学 ›› 2013, Vol. 33 ›› Issue (09): 1975-1981.DOI: 10.6023/cjoc201302018 上一篇    下一篇

研究论文

对甲苯磺酸催化的2-乙酰氧甲基吡咯衍生物和醇的醚化反应研究

严兆华, 余信权, 刘永杰, 许云, 林森   

  1. 南昌大学理学院化学系 南昌 330031
  • 收稿日期:2013-03-01 修回日期:2013-04-28 发布日期:2013-05-08
  • 通讯作者: 严兆华 E-mail:yanzh@ncu.edu.cn
  • 基金资助:

    江西省自然科学基金(No. 2009GZH0078)资助项目

Etherification of 2-Acetoxymethylpyrrole Derivative with Alcohol Catalyzed by para-Toluenesulfonic Acid

Yan Zhaohua, Yu Xinquan, Liu Yongjie, Xu Yun, Lin Sen   

  1. Department of Chemistry, Nanchang University, Nanchang 330031
  • Received:2013-03-01 Revised:2013-04-28 Published:2013-05-08
  • Supported by:

    Project supported by the Natural Science Foundation of Jiangxi Province (No. 2009GZH0078)

研究了对甲苯磺酸催化的2-乙酰氧甲基吡咯衍生物和醇之间的醚化反应, 结果以优秀的收率生成了相应的2-烷氧甲基吡咯衍生物. 该反应具有条件温和、产物得率高和后处理简单等优点, 提供了一种在弱酸条件下制备2-烷氧甲基吡咯衍生物的新方法, 提出了一种基于氮杂富勒烯过渡态的反应机理用于解释实验现象.

关键词: 2-乙酰氧甲基吡咯衍生物, 2-烷氧甲基吡咯衍生物, 醚化反应, 氮杂富勒烯,

Etherification of 2-acetoxymethylpyrrole derivatives with alcohols catalyzed by para-toluenesulfonic acid was investigated in details resulting in the smooth formation of the corresponding 2-alkoxymethylpyrrole derivatives in excellent yields. An alternate method for the preparation of 2-alkoxymethylpyrrole derivatives starting from 2-acetoxymethylpyrrole derivatives under weak acidic condition was provided. The main advantages of the developed methodology are mild reaction conditions, high yields of products and simple work-up procedure. A plausible mechanism involving the generation of highly reactive azafulvene intermediate 4 was proposed to explain the observed phenomena.

Key words: 2-acetoxymethylpyrrole derivative, 2-alkoxymethylpyrrole derivative, etherification, azafulvene, alcohol