论文总字数：18947字

摘 要

喹啉类衍生物是一类重要的杂环化合物，被广泛地应用于药物筛选、化学分析、染料工业等领域。因此，自从上个世纪初化学家们第一次发现喹啉的合成方法以来，如何用化学方法来合成喹啉类衍生物一直是有机合成化学家们研究的热点。虽然过渡金属催化合成喹啉衍生物避免了浓硫酸或浓盐酸的使用，但是存在着催化剂难分离回收的问题。因此，研究原子经济性的、绿色的喹啉类衍生物的新合成方法具有重大的意义。

本论文主要研究了以亚胺和丙炔酸甲酯为起始原料合成喹啉的方法。通过催化剂、溶剂和温度的筛选和优化，得出以三氯化铁作催化剂、二氯乙烷作溶剂，在加热回流条件下可获得较高收率的喹啉化合物。目标产物经氢谱和碳谱进行了结构表征。在优化条件下，我们合成出三种喹啉羧酸酯类化合物分别为：2-苯基-喹啉-3 -甲酸甲酯(2a)、6-甲氧基-2-苯基-喹啉-3-甲酸甲酯(2b)、6-氯-2 -苯基-喹啉-3-甲酸甲酯(2c)，它们的产率分别为82%、81%、73%。

该合成方法具有操作简单、反应温和、后处理方便，效率高等优点，为喹啉衍生物的合成方法提供了补充。

关键词： 亚胺、丙炔酸甲酯、喹啉衍生物

Abstract

Quinoline and its derivatives, which play an important role in the field of drug filtration, chemical analysis, dye industry, etc., are important organic heterocycles. Therefore, since the beginning of the last century, chemists found that the synthesis method of quinoline, how to use the chemical methods to synthesize quinoline and its derivatives has been the focus of synthetic organic chemistry. Although the transition metal catalyzed synthesis method is effective to avoid the high temperatures and strong acids, the transition metal catalyst still exists a series of deficiencies such as catalyst separation and recycling difficulties in the catalytic reaction process. Therefore, the study of the new atom economy, green synthetic method of quinoline and its derivatives is of great significance.

This paper studied the reaction of imines and methyl propiolate. The catalysts, solvents and the temperature were studied and optimized. The results showed that quinolines were obtained with high yields when using using FeCl₃ as the catalyst, and in the presence of 1,2-dichloroethane (DCE). The structures of the products were confirmed by ¹H NMR and ¹³C NMR. Under the optimized reaction, we synthesized three compounds, they were 2-phenylquinoline-3-carboxylate (2a), methyl 6-methoxy-2-phenylquinoline-3-carboxylate (2b) and methyl 6-chloro-2-phenylquinoline-3-carboxylate (2c), and their yields were 82%, 81%, 73% respectively.

The advantages of this method are operational simplicity, mild, efficient and so on, it offers a way to synthesize quinolines.

Keywords: Imines; Methyl propiolate; Quinolines derivatives

目 录

摘要.................................................................................................................................I

Abstract........................................................................................................................II

第一章 绪论 1

1.1 喹啉类化合物简介 1

1.1.1喹啉的结构及基本性质 1

1.1.2 喹啉及其衍生物的用途 1

1.2 喹啉的合成方法 3

1.2.1 传统合成方法 3

1.2.2 现代合成方法 6

1.2 本课题研究目的……………………………………………………………...8

第二章 实验部分 9

2.1 主要仪器及化学试剂 9

2.2 亚胺的制备 10

2.2.1 亚胺1的制备 10

2.2.2 不同取代基亚胺的制备 10

2.3 喹啉羧酸酯化合物的合成 11

2.3.1 喹啉羧酸酯2的制备 11

2.3.2 不同取代基喹啉羧酸酯的合成 11

2.4 产物结构表征 11

第三章 结果与讨论 13

3.1 合成喹啉羧酸酯的影响因素 13

3.1.1 催化剂对反应的影响 13

3.1.2 溶剂对反应的影响 14

3.1.3 温度对反应的影响 14

3.2 取代基对喹啉羧酸酯合成的影响 15

第四章 结论与展望 16

4.1 结论 16

4.2 展望 16

参考文献 17

附录 20

致谢 23

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