吡咯2甲醇酯类化合物的醚化反应研究有机化学专业论文.docxVIP

摘要摘要 摘要 摘要 吡咯类杂环化合物在有机化学和药物化学领域中具有重要的地位，因此正 受到人们高度的重视。在合成吡咯类潜在药物分子过程中，我们发现并研究的 两类醚化反应均是吡咯类化合物所特有的，到目前为止，还未见文献报道。这 两类醚化反应的反应条件温和，操作简单易行，转化产率高，具有广泛的适用 性，因此必将拓展有机化学尤其是吡咯化学的知识领域和丰富醚类化合物的制 各方法，而且在有机合成化学当中也将发挥一定的作用。本论文系统研究了吡 咯．2．甲醇酯类化合物的两类醚化反应的反应条件、适用范围和反应机理，共包 括以下三章： 第1章，综述了醚类化合物的制备方法。 第2章，系统研究了吡咯．2．甲醇酯类化合物在对甲苯磺酸催化下与醇发生 的醚化反应。首先考察了此类反应的反应条件及适用范围，发现吡咯．2．甲醇酯 类化合物与醇的醚化反应与吡咯环中N上的取代基并无关系，并且不适用于叔 醇；其次根据实验现象和实验结果提出了可能的反应机理。 第3章，系统研究了吡咯．2．甲醇酯类化合物在醇溶液中与醇钠的醚化反应。 首先考察了此类反应的反应条件及适用范围，发现吡咯．2．甲醇酯类化合物与醇 钠的醚化反应与吡咯环中N上的H紧密相关，但同样地不适用于叔醇钠和二元 醇钠；其次根据实验现象和实验结果提出了可能的反应机理。 关键词：吡咯．2．甲醇酯类化合物；醇；对甲苯磺酸；醚化反应；醇钠 II Abstract Abstract Abstract Pyrrole compounds have received a great deal of attention,due to their importance in organic chemistry and pharmaceutical chemistry．In the course of study on the synthesis of pyrrole compounds pocessing potential bioactivity,we found two novel types of etherification of 2-acyloxymethylpyrrole compounds with alcohols catalyzed by pqoluenesulfonic acid and with sodium alkoxide in corresponding alcohol，which have the advantages of mild reaction condition,higll yields，labile work—up，and broad application scope．Therefore，Our results will contribute to broadening the knowledge of pyrrole chemistry，offering an alternate preparation method of ether．In this thesis，the optimization of reaction conditions，application scope and mechanism of etherification of acetic acid pyrrol-·2·-ylmethyl ester compound will be described．It contains three chapters aS belows： In chapter one，the preparation of ethers were reviewed． In chapter two，the etherification of 2-acyloxymethylpyrrole compounds with alcohols in the presence of P．toluene sulfonic acid as catalyst was described in detail．We frstly optimized the reaction conditions and studied its application scope． We found substituent on the N atom of the pyrrole ring has 110 effect on the etherification and tert-alcohols are not suitable for this reaction．Then,we proposed a reasonable mechanism to interpret the etherification based on