过渡金属催化叠氮与炔的环化反应及其在有机合成中的应用
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摘要
叠氮化合物是一类很重要的有机合成中间体,可以和很多有机化合物反应生成含氮的化合物,尤其近年来叠氮化合物与炔反应的文献报道最多,应用也相当广泛。本论文主要研究过渡金属催化的叠氮化合物与炔的环化反应及其在有机合成中的应用,主要包括以下内容：
第一章对近几年来叠氮与炔的环化反应及其应用给出了综述。主要总结了传统的Huigen反应,Cu(1)催化的及其它金属参与的Huigen反应合成各种取代三唑,磺酰叠氮与炔参与的多组分反应合成一系列含氮有机化合物,分子内叠氮与炔的环化反应合成杂环。在这些反应中应用最多的就是Cu(1)催化的叠氮与炔的环加成反应(简称CuAAC),就其应用作了简单的总结。
第二章中首先简单介绍了近年来手性氨基醇在硼烷参与的前手性酮不对称还原反应的研究。利用分子间CuAAC反应,设计了1,2,3-三唑功能化的C3对称手性氨基醇配体,应用在硼烷参与的前手性酮不对称还原中。研究表明,该类型的催化剂具有良好的催化活性,最重要的是该催化剂很容易从反应体系中沉淀出来,经过简单的洗涤,干燥即可循环使用,该催化剂可重复循环使用四次,催化活性没有明显的降低。
第三章中利用银催化分子内有机叠氮与炔的环化反应合成1,3-二取代的异喹啉或单取代的异喹啉。首先对异喹啉的研究进展作了总结。然后我们对反应的条件进行了筛选和优化,并对该反应的底物进行了的扩展.讨论芳环取代基上电子效应对反应的影响,并提出了一个合理的反应机理。结果表明,该反应在催化量AgSbF6和2 equivTFA的作用下,在DCE中80℃可合成取代的异喹啉。反应条件温和,操作简单,产率良好。
Azide is a kind of very important organic intermediate. It can react with organic compounds to afford many nitrogen-containing compounds. The azide-alkyne cyclization reaction have been received much attention in recent years and widely found application in many fields. In this paper, we are interested in the transition metal-catalyzed azide and alkyne cyclization reaction and its application in organic synthesis, which including the following:
In the first chapter, we have reviewed the recent studies about the azide-alkyne cyclization reaction and its application. We have summarized the Huigen reaction, such as the traditional Huisgen reaction, Cu(1)-catalyzed Huisgen reaction, and other metals-catalyzed Huisgen reaction to synthsize a variety of subsitituted triazoles. We have also summarized sulfonyl azide and alkyne-involved multi-component reactions, and intramolecular azide-alkyne cyclization reactions. In these reactions, Cu (1)-catalyzed azide and alkyne cycloaddition reactions (CuAAC) have been widely used in many fields, and we also have given a brief summary on its application.
In Chapter II, First, we have reviewd the studies on the the chiral amino alcohols, which had been used in the borane-mediated reduction of prochiral ketones. We have synthesized 1,2,3-triazole-functionalized, C3-symmetric chiral amino alcohol catalysts via CuAAC reaction. Those catalysts have been used in the borane-mediated reduction of prochiral ketones. The results showed that the catalysts had good catalytic activity, and it could easily precipitate out from the reaction mixture and be reused after a simple washing and drying. The catalyst can be reused four times, without obvious decrease of catalytic activity.
In Chapter III, we have developed the Ag-catalyzed intramolecular organic azide and alkyne cyclization to synthesize of 1,3-disubstituted isoquinolines or non-substituted isoquinolines. Firstly, we have reviewed the recent stuides on isoquinoline synthesis. Sencondly, the reaction conditions were optimized, and the scope of this reaction was investigated. Thirdly, we have also discussed the electronoc effect of substituents on the aromatic ring and proposed a resonable reaction mechanism. The results showed that the substituted isoquinoline could be synthesized in catalytic amount AgSbF6(20%) and 2 equiv TFA in the DCE at 80℃. The reaction afforded good to excellent yields under mild and simple conditions.
第一章对近几年来叠氮与炔的环化反应及其应用给出了综述。主要总结了传统的Huigen反应,Cu(1)催化的及其它金属参与的Huigen反应合成各种取代三唑,磺酰叠氮与炔参与的多组分反应合成一系列含氮有机化合物,分子内叠氮与炔的环化反应合成杂环。在这些反应中应用最多的就是Cu(1)催化的叠氮与炔的环加成反应(简称CuAAC),就其应用作了简单的总结。
第二章中首先简单介绍了近年来手性氨基醇在硼烷参与的前手性酮不对称还原反应的研究。利用分子间CuAAC反应,设计了1,2,3-三唑功能化的C3对称手性氨基醇配体,应用在硼烷参与的前手性酮不对称还原中。研究表明,该类型的催化剂具有良好的催化活性,最重要的是该催化剂很容易从反应体系中沉淀出来,经过简单的洗涤,干燥即可循环使用,该催化剂可重复循环使用四次,催化活性没有明显的降低。
第三章中利用银催化分子内有机叠氮与炔的环化反应合成1,3-二取代的异喹啉或单取代的异喹啉。首先对异喹啉的研究进展作了总结。然后我们对反应的条件进行了筛选和优化,并对该反应的底物进行了的扩展.讨论芳环取代基上电子效应对反应的影响,并提出了一个合理的反应机理。结果表明,该反应在催化量AgSbF6和2 equivTFA的作用下,在DCE中80℃可合成取代的异喹啉。反应条件温和,操作简单,产率良好。
Azide is a kind of very important organic intermediate. It can react with organic compounds to afford many nitrogen-containing compounds. The azide-alkyne cyclization reaction have been received much attention in recent years and widely found application in many fields. In this paper, we are interested in the transition metal-catalyzed azide and alkyne cyclization reaction and its application in organic synthesis, which including the following:
In the first chapter, we have reviewed the recent studies about the azide-alkyne cyclization reaction and its application. We have summarized the Huigen reaction, such as the traditional Huisgen reaction, Cu(1)-catalyzed Huisgen reaction, and other metals-catalyzed Huisgen reaction to synthsize a variety of subsitituted triazoles. We have also summarized sulfonyl azide and alkyne-involved multi-component reactions, and intramolecular azide-alkyne cyclization reactions. In these reactions, Cu (1)-catalyzed azide and alkyne cycloaddition reactions (CuAAC) have been widely used in many fields, and we also have given a brief summary on its application.
In Chapter II, First, we have reviewd the studies on the the chiral amino alcohols, which had been used in the borane-mediated reduction of prochiral ketones. We have synthesized 1,2,3-triazole-functionalized, C3-symmetric chiral amino alcohol catalysts via CuAAC reaction. Those catalysts have been used in the borane-mediated reduction of prochiral ketones. The results showed that the catalysts had good catalytic activity, and it could easily precipitate out from the reaction mixture and be reused after a simple washing and drying. The catalyst can be reused four times, without obvious decrease of catalytic activity.
In Chapter III, we have developed the Ag-catalyzed intramolecular organic azide and alkyne cyclization to synthesize of 1,3-disubstituted isoquinolines or non-substituted isoquinolines. Firstly, we have reviewed the recent stuides on isoquinoline synthesis. Sencondly, the reaction conditions were optimized, and the scope of this reaction was investigated. Thirdly, we have also discussed the electronoc effect of substituents on the aromatic ring and proposed a resonable reaction mechanism. The results showed that the substituted isoquinoline could be synthesized in catalytic amount AgSbF6(20%) and 2 equiv TFA in the DCE at 80℃. The reaction afforded good to excellent yields under mild and simple conditions.
引文
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