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有机化学.pdfVIP

DOI: 10.6023/cjoc201302018 研究论文 有机化学 Chinese Journal of Organic Chemistry ARTICLE 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 (南昌大学理学院化学系 南昌 330031) 摘要 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; 醇 Etherification of 2-Acetoxymethylpyrrole Derivative with Alcohol Catalyzed by para-Toluenesulfonic Acid Yan, Zhaohua* Yu, Xinquan Liu, Yongjie Xu, Yun Lin, Sen (Department of Chemistry, Nanchang University, Nanchang 330031) Abstract 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. Keywords 2-acetoxymethylpyrrole derivative; 2-alkoxymethylpyrrole derivative; etherification; azafulvene; alcohol 2-烷氧甲基吡咯衍生物正日益受到人们的重视. 近 强酸性和高温条件下很容易聚合或者不稳定易于分解. 年来, 人们发现许多天然产物中含有 2-烷氧甲基吡咯片 因此现有的制备 2-