摘     要:吲哚骨架经常在许多重要的天然产物和手性药物中被发现，其中，2-取代吲哚在药物应用方面显示出了巨大的潜力，这种类型的结构也是许多生物活性分子的核心结构。Friedel-Crafts烷基化反应是合成吲哚衍生物最重要的反应之一，然而，由于C3位的亲核性较高，大多数这些转化主要集中在吲哚的C3位置上。相比之下，在反应活性较低的C2位置发生Friedel-Crafts烷基化反应，以合成具有C2-苄型立体中心的吲哚，这种反应却很少被利用，但是它们经常出现在许多生物活性分子和天然产物中，是重要的结构基元。因此，非常希望开发吲哚的高效Friedel-Crafts C2-烷基化反应。为此目的，吲哚的Pictet-Spengler反应已经确立，通过引入4,7-二氢吲哚的Friedel-Crafts烷基化和随后的氧化，也得到期望的产物，但它本质上局限于分子内的形式。3-取代吲哚的直接C2-烷基化是合成2-取代吲哚的非常有前途的途径，但它仍然是一个挑战。因此，本课题致力于研究3-取代的吲哚和亚胺类化合物的加成反应,为直接合成2-取代吲哚衍生物提供一种参考。本论文主要分为两个部分：

第一部分：文献综述。介绍了2-取代吲哚化合物常用的合成方法。(1) 吲哚的Pictet-Spengler反应； (2) 吲哚的直接Friedel-Crafts- C2-烷基化反应。

第二部分：合成2-取代吲哚化合物的研究。详细的描述了实验步骤以及一系列的底物拓展和反应优化，并给出了数据表征和结论。

关键词：吲哚衍生物；Friedel-Crafts烷基化反应

Abstract:Skeleton skeletons are often found in many important natural products and chiral drugs. Among them, 2-substituted anthraquinones show great potential in drug applications. This type of structure is also the core structure of many bioactive molecules. The Friedel-Crafts alkylation reaction is one of the most important reactions for the synthesis of anthraquinone derivatives. However, due to the higher nucleophilicity of the C3 position, most of these transformations are mainly concentrated on the C3 position of the oxime. In contrast, the Friedel-Crafts alkylation reaction takes place at the less reactive C2 position to synthesize quinones with C2-benzyl stereocenters. This reaction is seldom used, but they often appear in many Bioactive molecules and natural products are important structural motifs. Therefore, it is highly desirable to develop an efficient Friedel-Crafts C2-alkylation reaction of hydrazine. For this purpose, the Pictet-Spengler reaction of niobium has been established. By introducing Friedel-Crafts alkylation of 4,7-dihydroanthracene and subsequent oxidation, the desired product is also obtained, but it is inherently restricted to intramolecular form. The direct C2-alkylation of 3-substituted anthracenes is a very promising approach to the synthesis of 2-substituted anthraquinones, but it remains a challenge. Therefore, this topic is devoted to the study of the addition reaction of 3-substituted fluorenes and imines, providing a reference for the direct synthesis of 2-substituted fluorene derivatives.

This paper is pided into two parts:

Part 1: Literature review. A synthetic method commonly used in 2-substituted hydrazine compounds was introduced. (1) Pictet-Spengler reaction; (2) Direct Friedel-Crafts-C2-Alkylation of Gallium.

Part II: Study on synthesis of 2-substituted hydrazine compounds. Detailed description of the experimental steps and a series of substrate development and reaction optimization, and gives data characterization and conclusions.

Key words: Indol;  Friedel-Crafts alkylation

目   录

摘  要 2

目  录 4

引  言 5

正  文 6

1 文献综述 6

1.1 2-取代吲哚衍生物的合成方法 6

1.1.1  吲哚的Pictet-Spengler反应 6

1.1.2  吲哚的直接Friedel-Crafts- C2-烷基化反应 7