Cu（Ⅰ）催化的1，2，3-三唑的合成及其应用研究
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摘要
1，2，3-三唑类化合物是一类重要的杂环化合物，自其被发现至今，大量的实验表明，该类化合物具有独特化学性质和药用价值，因而受到了广泛的关注，在有机化学、有机金属化学、药物化学和材料化学等诸多领域具有广阔的应用前景。本论文针对1，2，3-三唑的合成和应用，主要包括以下方面：
第一章对近几年来1，2，3-三唑合成研究进行了概述，总结了有机叠氮和炔烃、烯烃的1，3-偶极环加成反应(Huisgen反应)以及其他方法合成三唑的进展。其中主要介绍了Cu(Ⅰ)催化下有机叠氮和末端炔在合成1，4-二取代，1，4，5-三取代-1，2，3-三唑合成研究工作。相对于传统Huisgen反应，Cu(Ⅰ)催化下反应具有条件温和，高产率和高区域选择性的优势。
第二章中首先简单介绍了单1-取代-1，2，3-三唑研究历史。对比以往研究的特点和Cu(Ⅰ)催化下Huisgen反应的优势，我们提出了Cu(Ⅰ)催化下有机叠氮和乙炔气体常压室温下合成单1-取代-1，2，3-三唑的方法。对反应条件完成了筛选和优化，并对该反应的应用范围进行了的扩展。实验表明，该反应在催化量CuI/Et_3N的作用下，适用于系列单1-取代-1，2，3-三唑的合成。反应条件温和，操作简单，产率良好。
第三章介绍了Cu(Ⅰ)催化下Huisgen反应在广泛应用的背景下，结合有机小分子催化剂和离子液体负载合成的特点，成功利用Cu(Ⅰ)催化下Huisgen反应，合成了离子液体负载的有机小分子。该负载的催化剂在酮和β-取代硝基烯的直接Micheal反应表现出了良好的反应活性，且由于离子液体的性质的影响，使得该催化剂的回收与利用变得相当方便。该催化剂可重复循环使用四次，催化活性没有明显的降低。
The 1,2,3-triazoles, as important heterocyclic compounds, hase been known formore than one hundred years. Due to their unique chemical and structural properties,they have received much attention over the past decades and found wide applicationin organic chemistry, organometallic chemistry, medicinal chemistry and materialscience. We are interesting in the synthesis and the application of 1,2,3-triazoles inthis paper, which including the following:
In the first chapter, we reviewed mainly the development of Huisgen's 1,3-dipolar[3+2]-cycloaddition from organoazides and alkynes or alkenes to synthize1,2,3-triazoles in recent years. Since Cu(I)-catalyzed Huisgen reaction has reported asan useful process to connect diverse building blocks of organoazides and alkynes, thereaction has made great progress in the synthesis of 1,4-disubstituted and1,4,5-trisubstituted 1,2,3-triazol-synthesis researchs. Compared with traditionalHuisgen reaction, Cu(I)-catalyzed Huisgen reaction are mild-conditions, high yieldand high regioselectivity. At the same time, others transitional-metals were used in thesynthesis of triazoles.
In chapterⅡ, a summary of 1-monosubstituded-1,2,3-triazole was introducedbriefly. Against previous researches, Cu(I)-catalyzed Huisgen reaction wasimplemented from organoazides and acetylene gas under normal pressure at roomtemperature. The screening and optimization of the experimental conditions showedthat CuI/Et_3N in catalytic amount and dimethyl sulfoxide (DMSO) is essencial to givethe good results.
The third chapter is devoted to the combination of the Cu(I)-catalyzed Huisgenreaction, organocatalysts and ionic-liquid supported synthesis. From Cu(I)-catalyzedHuisgen reaction, an ionic-liquid-supported organocatalyst was synthesizedsuccessfully. The ionic-liquid-supported organocatalyst shown the good catalyticalactivity in the direct Michael addition of ketone withβ-nitroalkene. The ionic-liquid-supported organocatalyst could recyclization and reuse facilely, and infour times of reuses, no significant loss of catalytic activity was found.
第一章对近几年来1，2，3-三唑合成研究进行了概述，总结了有机叠氮和炔烃、烯烃的1，3-偶极环加成反应(Huisgen反应)以及其他方法合成三唑的进展。其中主要介绍了Cu(Ⅰ)催化下有机叠氮和末端炔在合成1，4-二取代，1，4，5-三取代-1，2，3-三唑合成研究工作。相对于传统Huisgen反应，Cu(Ⅰ)催化下反应具有条件温和，高产率和高区域选择性的优势。
第二章中首先简单介绍了单1-取代-1，2，3-三唑研究历史。对比以往研究的特点和Cu(Ⅰ)催化下Huisgen反应的优势，我们提出了Cu(Ⅰ)催化下有机叠氮和乙炔气体常压室温下合成单1-取代-1，2，3-三唑的方法。对反应条件完成了筛选和优化，并对该反应的应用范围进行了的扩展。实验表明，该反应在催化量CuI/Et_3N的作用下，适用于系列单1-取代-1，2，3-三唑的合成。反应条件温和，操作简单，产率良好。
第三章介绍了Cu(Ⅰ)催化下Huisgen反应在广泛应用的背景下，结合有机小分子催化剂和离子液体负载合成的特点，成功利用Cu(Ⅰ)催化下Huisgen反应，合成了离子液体负载的有机小分子。该负载的催化剂在酮和β-取代硝基烯的直接Micheal反应表现出了良好的反应活性，且由于离子液体的性质的影响，使得该催化剂的回收与利用变得相当方便。该催化剂可重复循环使用四次，催化活性没有明显的降低。
The 1,2,3-triazoles, as important heterocyclic compounds, hase been known formore than one hundred years. Due to their unique chemical and structural properties,they have received much attention over the past decades and found wide applicationin organic chemistry, organometallic chemistry, medicinal chemistry and materialscience. We are interesting in the synthesis and the application of 1,2,3-triazoles inthis paper, which including the following:
In the first chapter, we reviewed mainly the development of Huisgen's 1,3-dipolar[3+2]-cycloaddition from organoazides and alkynes or alkenes to synthize1,2,3-triazoles in recent years. Since Cu(I)-catalyzed Huisgen reaction has reported asan useful process to connect diverse building blocks of organoazides and alkynes, thereaction has made great progress in the synthesis of 1,4-disubstituted and1,4,5-trisubstituted 1,2,3-triazol-synthesis researchs. Compared with traditionalHuisgen reaction, Cu(I)-catalyzed Huisgen reaction are mild-conditions, high yieldand high regioselectivity. At the same time, others transitional-metals were used in thesynthesis of triazoles.
In chapterⅡ, a summary of 1-monosubstituded-1,2,3-triazole was introducedbriefly. Against previous researches, Cu(I)-catalyzed Huisgen reaction wasimplemented from organoazides and acetylene gas under normal pressure at roomtemperature. The screening and optimization of the experimental conditions showedthat CuI/Et_3N in catalytic amount and dimethyl sulfoxide (DMSO) is essencial to givethe good results.
The third chapter is devoted to the combination of the Cu(I)-catalyzed Huisgenreaction, organocatalysts and ionic-liquid supported synthesis. From Cu(I)-catalyzedHuisgen reaction, an ionic-liquid-supported organocatalyst was synthesizedsuccessfully. The ionic-liquid-supported organocatalyst shown the good catalyticalactivity in the direct Michael addition of ketone withβ-nitroalkene. The ionic-liquid-supported organocatalyst could recyclization and reuse facilely, and infour times of reuses, no significant loss of catalytic activity was found.
引文
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