钯催化分子内吲哚碳氢键对氰基的加成反应研究

发布时间：2018-06-16 20:29

本文选题：钯催化 + 碳氢官能团化　；参考：《吉林大学》2017年硕士论文

【摘要】：过渡金属催化的sp~2碳氢键与碳碳多键的环化反应是一种高效的构建环状化合物的方法,并且在现代有机化学中占有非常重要的地位。与此相比,过渡金属催化的碳氢键对极性不饱和碳杂键例如氰基的加成反应却较少受到关注。具有六元并环结构的吲哚衍生物例如咔唑、四氢咔唑、吡啶并[1,2-a]吲哚,代表了一类重要的具有潜在生物活性的杂环化合物。除此之外,相应的七八元环的吲哚并环结构也常见于多种天然产物和药物分子中。因此合成吲哚并环衍生物具有非常重要的意义。本论文中我们报道了一种钯催化具有氰醇结构单元的吲哚经由分子内碳氢键对氰基的加成环化反应,合成一系列吲哚并环类化合物的方法。主要研究内容如下:(1)我们发展了一种以C(3),C(2),N(1)位具有氰醇结构单元的吲哚为原料经由钯催化分子内碳氢键对氰基的加成环化反应,多样性地合成吲哚多并环化合物的方法。在最优的反应条件下,以中等到高产率合成了一系列官能团化的吡啶并[1,2-a]吲哚,四氢咔唑和吲哚并七、八元环的化合物。(2)我们发展了一种以C(3),C(2)具有氰醇结构单元的吲哚为原料经由钯催化分子内碳氢键对氰基的加成环化反应制备氨基咔唑类化合物的方法。在最优的反应条件下,以中等到较高产率合成了一系列官能团化的2-氨基咔唑和5-氨基咔唑。
[Abstract]:Transition metal-catalyzed cyclization of sp~2 and carbon-carbon bonds is an efficient method for the construction of cyclic compounds and plays an important role in modern organic chemistry. In contrast, the addition of transition metal-catalyzed carbon-hydrogen bonds to polar unsaturated carbon heterodynes, such as cyanide, has attracted less attention. Indole derivatives with hexagonal acyclic structure, such as carbazole, tetrahydrocarbazole and pyridino [1h2a] indole, represent a class of important heterocyclic compounds with potential biological activity. In addition, the indolo ring structure of the seven-and-eight-member ring is also common in many natural products and drug molecules. Therefore, the synthesis of indole ring derivatives is of great significance. In this paper, we report a palladium catalyzed cyclization of indoles with cyanocyclization via intramolecular carbon and hydrogen bonds to synthesize a series of indole cyclized compounds. The main research contents are as follows: (1) We have developed a method for synthesizing indolepolycyclic compounds by palladium catalyzed addition cyclization of cyanide with cyclization of intramolecular carbon and hydrogen bonds from indoles with cyanohydrin structure units at the C ~ (3 +) C ~ (2 +) C ~ (2 +) ~ (2 +) position (C _ (3) C _ (2) C _ (2) C _ (1) as raw materials. Under the optimum reaction conditions, a series of functionalized pyridino [1o 2-a] indole, tetrahydrocarbazole and indole 7 were synthesized in medium to high yield. We have developed a palladium catalyzed addition cyclization reaction of carbon and hydrogen bond to cyanide from indoles with cyanoalcohol structure unit to prepare aminocarbazole compounds from C ~ (3 +) C ~ (2 +) C _ (2) C _ (2) C _ (2) C _ (2) C _ (3) C _ (2) with cyclization of carbon and hydrogen bond to cyanide catalyzed by palladium. Under the optimum reaction conditions, a series of functionalized 2-aminocarbazole and 5-aminocarbazole were synthesized at medium to high yield.
【学位授予单位】：吉林大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O621.251

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