【作者】 张丽莉；

【导师】 郭佃顺；

【作者基本信息】 山东师范大学 ， 有机化学， 2012， 硕士

【摘要】 1,2,3-三唑类化合物是一类重要的含氮五元杂环化合物，具有独特的结构和化学性质，被广泛应用于药物研发、材料科学和精细化学品等诸多领域。因此，1,2,3-三唑衍生物的高效合成研究越来越受到人们的关注。本论文开展了基于Benedict试剂催化的有机叠氮化合物与末端炔的click反应研究，主要分为以下两个部分：第一章全面总结了以叠氮有机化合物和末端炔通过Huisgen 1,3-偶极环加成反应合成1,2,3-三唑化合物的研究进展，其中重点介绍了各种铜催化的Huisgen环加成反应，即click反应。铜（I）催化的Huisgen反应，具有条件温和，产率高和区域选择性高的优点。第二章系统研究了Benedict试剂催化的Huisgen环加成反应，首先优化了Benedict试剂中各组分的最佳比例和还原剂的种类，并探索了催化剂的用量、反应溶剂、反应温度等对Huisgen环加成反应的影响，确定了最佳反应条件：40oC，5 mol % IBR（改进的Benedict试剂），5 mol %果糖（还原剂），水（溶剂）。最后利用优化的反应条件考查不同有机叠氮化合物与各种末端炔的环加成反应，成功合成了一系列1,2,3-三唑化合物。此外，还研究了某些体系的三组分（苄基卤代烃、叠氮化钠和末端炔）一锅反应。本论文开发的Benedict试剂催化Huisgen环加成反应技术，拓宽了1,2,3-三唑化合物的合成方法，对药物和新材料的合成具有重要的意义。更多还原

【Abstract】 1,2,3-Triazoles are important five-membered N-heterocyclic compounds due totheir unique chemical and structural properties. They were widely used in many areassuch as drug discovery, materials science and fine chemicals. Therefore, efficientsyntheses of 1,2,3-triazoles have attracted considerable attention. In this dissertation, anew catalytic system used for Huisgen 1,3-dipolar cycoladdition has been developedbased on Benedict’s reagent, which can apply to prepare 1,2,3-triazoles.In the first section, the recent development of Huisgen 1,3-dipolar cycoladditionof organoazides and alkynes offering 1,2,3-triazoles was reviewed briefly. Comparedwith traditional Huisgen cycoladdition, Cu(I) catalyzed Huisgen reaction possessesmild-condition, high yield and high regioselectivity. While other transition metalmediated Huisgen 1,3-dipolar cycoladditions were also summarized.In the second section, Benedict’s reagent was proposed as an efficient catalyst forazide-alkyne cycloaddition. Firstly, the molar ratio of Benedict’s reagent componentsand its catalytic loading were optimized through the model reaction. Secondly, theoptimal reaction conditions were obtained, involving 5 mol% of IBR (improvedBenedict’s reagent) and 5 mol% of fructose (reductant) in H2O (solvent) at 40°C.Thirdly, the scope of Benedict’s reagent catalyzed 1,3-dipolar cycloaddition reactionof diverse organic azides and alkynes was investigated. A series of corresponding1,2,3-triazole compounds were obtained in excellent yields. In addition, benzyl halides,NaN3and alkynes also could be converted into 1,4-disubstituted 1,2,3-triazoles by aconvenient one-pot three-component reaction.In summary, the studies on the Huisgen cycloaddition reaction catalyzed byBenedict’s reagent are of significance for exploring new synthetic method of1,2,3-triazoles, drug discovery as well as materials science.更多还原