CuI催化芳基叠氮化合物的光环化反应研究
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摘要
本论文主要论述了有机叠氮化合物的研究工作,包含以下两章内容。
第-章,对有机叠氮化合物作了简单的介绍,包括这类特殊化合物的基本性质,常用的制备方法以及他们的化学反应,其中着重介绍了他们的光化学反应(环加成反应,氮烯化学,插入反应,重排反应和金属催化反应)及其在有机合成化学中的应用,同时对此类化合物的最新研究进展进行了简单的介绍。
第二章,介绍了已经完成的-些研究工作。包括：(1)研究了3-(2-叠氮苯亚甲叉)-取代的内酰胺类化合物(包括3-(2-叠氮苯亚甲叉)-吲哚酮类化合物,3-(2-叠氮苯亚甲叉)-吡咯酮类化合物,3-(2-叠氮苯亚甲叉)-吡唑酮类化合物,4-(2-叠氮苯亚甲叉)-3-苯基-1,3-异喹啉二酮和5-(2-叠氮苯亚甲叉)-1,3-二甲基嘧啶-2,4,6-三酮)的光化学反应和热化学反应。通过对他们的研究我们发展了-种新的合成多环吲哚类化合物的方法,如吲哚[3,2-c]喹啉-6-酮类化合物,吡啶[4,3-b]吲哚-1-酮类化合物,嘧啶[4,5-b]吲哚-4-酮类化合物和其他吲哚类化合物。该方法产率较高,反应条件温和。(2)研究了1-(2-叠氮苯亚甲叉)取代的茚类化合物和(2-叠氮苯亚甲叉)取代的羰基化合物(包括2-(2-叠氮苯亚甲叉)苯并呋喃-3-酮,2-(2-叠氮苯亚甲叉)-1,3-茚二酮,3-(2-叠氮苯亚甲叉)苯并呋喃-2-酮,2-(2-叠氮苯亚甲叉)-5,5-二甲基-1,3-环己二酮)的光环化反应,合成了一些新的苯并咔唑类稠合吲哚类衍生物。
This thesis deals with the studies on organic azides. It is divided into two chapters.
Chapter1describes basic properties, preparation methods and main chemistry reactions of organic azides. It focuses on their photochemiscal reactions including cycloadditions, nitrene chemistry, insertion reactions, rearrangement reactions and metal-catalysis reactions, and the application of these reactions in the organic synthesis.
Chapter2reports my research works on the photochemistry of organic azides. Firstly, the CuI-catalyzed photoreaction and thermal reactions of3-(2-azido-benzylidene)-lactams have been investigated. The studied lactams are3-(2-azidobenzylidene) indol-2-ones,3-(2-azidobenzylidene)pyrrol-2-ones,4-(2-azido-benzylidene)pyrazol-5-ones,4-(2-azidobenzylidene)-2-phenylisoquinoline-1,3(2H,4H)-dione, and5-(2-azido benzylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione. A new method for the synthesis of fused indole compounds, such as indolo[3,2-c]quinolin-6-ones, pyrido[4,3-b]indol-1-ones, pyridazino[4,5-b]indol-1-ones, dihydroindolo[3,2-d][2]benzazepin-5,7-dione, and [1,3]diazepino[5,6-b] indole-1,3,5-trione, has been developed by the photochemical and thermal cyclization-rearrangement reactions. It is an efficient method that is embodied under mild reaction condition and in high reaction yields. Secondly, the studies on the photoreaction of other3-(2-azidobenzylidene)-substituted compounds, such as1-(2-azidobenzylidene)-1H-indenes and2-(2-azidobenzylidene)-ones have been introduced. Benzocarbazoles and other fused indole derivatives have also been synthesized.
第-章,对有机叠氮化合物作了简单的介绍,包括这类特殊化合物的基本性质,常用的制备方法以及他们的化学反应,其中着重介绍了他们的光化学反应(环加成反应,氮烯化学,插入反应,重排反应和金属催化反应)及其在有机合成化学中的应用,同时对此类化合物的最新研究进展进行了简单的介绍。
第二章,介绍了已经完成的-些研究工作。包括：(1)研究了3-(2-叠氮苯亚甲叉)-取代的内酰胺类化合物(包括3-(2-叠氮苯亚甲叉)-吲哚酮类化合物,3-(2-叠氮苯亚甲叉)-吡咯酮类化合物,3-(2-叠氮苯亚甲叉)-吡唑酮类化合物,4-(2-叠氮苯亚甲叉)-3-苯基-1,3-异喹啉二酮和5-(2-叠氮苯亚甲叉)-1,3-二甲基嘧啶-2,4,6-三酮)的光化学反应和热化学反应。通过对他们的研究我们发展了-种新的合成多环吲哚类化合物的方法,如吲哚[3,2-c]喹啉-6-酮类化合物,吡啶[4,3-b]吲哚-1-酮类化合物,嘧啶[4,5-b]吲哚-4-酮类化合物和其他吲哚类化合物。该方法产率较高,反应条件温和。(2)研究了1-(2-叠氮苯亚甲叉)取代的茚类化合物和(2-叠氮苯亚甲叉)取代的羰基化合物(包括2-(2-叠氮苯亚甲叉)苯并呋喃-3-酮,2-(2-叠氮苯亚甲叉)-1,3-茚二酮,3-(2-叠氮苯亚甲叉)苯并呋喃-2-酮,2-(2-叠氮苯亚甲叉)-5,5-二甲基-1,3-环己二酮)的光环化反应,合成了一些新的苯并咔唑类稠合吲哚类衍生物。
This thesis deals with the studies on organic azides. It is divided into two chapters.
Chapter1describes basic properties, preparation methods and main chemistry reactions of organic azides. It focuses on their photochemiscal reactions including cycloadditions, nitrene chemistry, insertion reactions, rearrangement reactions and metal-catalysis reactions, and the application of these reactions in the organic synthesis.
Chapter2reports my research works on the photochemistry of organic azides. Firstly, the CuI-catalyzed photoreaction and thermal reactions of3-(2-azido-benzylidene)-lactams have been investigated. The studied lactams are3-(2-azidobenzylidene) indol-2-ones,3-(2-azidobenzylidene)pyrrol-2-ones,4-(2-azido-benzylidene)pyrazol-5-ones,4-(2-azidobenzylidene)-2-phenylisoquinoline-1,3(2H,4H)-dione, and5-(2-azido benzylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione. A new method for the synthesis of fused indole compounds, such as indolo[3,2-c]quinolin-6-ones, pyrido[4,3-b]indol-1-ones, pyridazino[4,5-b]indol-1-ones, dihydroindolo[3,2-d][2]benzazepin-5,7-dione, and [1,3]diazepino[5,6-b] indole-1,3,5-trione, has been developed by the photochemical and thermal cyclization-rearrangement reactions. It is an efficient method that is embodied under mild reaction condition and in high reaction yields. Secondly, the studies on the photoreaction of other3-(2-azidobenzylidene)-substituted compounds, such as1-(2-azidobenzylidene)-1H-indenes and2-(2-azidobenzylidene)-ones have been introduced. Benzocarbazoles and other fused indole derivatives have also been synthesized.
引文
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