摘要本文通过改变13种取代的苯甲醛，分别与5-氨基苯并咪唑和1,3-环戊二酮反应，无需加入任何的催化剂，在无水乙醇回流的条件下，即可合成一系列10-芳基-6,7,8,10-四氢化环戊基并[b]咪唑并[4,5-f]喹啉-9(1H)-酮衍生物。5-氨基苯并咪唑的4-位参与反应说明该反应具有很好的区域选择性，为咪唑并喹啉衍生物的合成提供了很好的方法。42173

该论文有图26幅，表1个，参考文献14篇。

毕业论文关键词：咪唑并喹啉  5-氨基咪唑  区域选择性  1,3-环戊二酮  合成

Synthesis of cyclopentaimidazoquinoline derivatives via a three-component reaction

Abstract

Thirteen kinds of substituted benzaaldehydes were used as the reactants to react with 1H-benzo[d]imidazol-5-amine, and cyclopentane-1,3-dione, respectively. This reaction was treated in refluxing EtOH without adding catalysts, and gave a series of 10-aryl-6,7,8,10-tetrahydrocyclopenta[b]imidazo[4,5-f]quinolin-9(1H)-one derivatives. It was confirmed that it was the 4-position in 1H-benzo[d]imidazol- 5-amine attending the reaction which indicated that this reaction had a good region-selectivity. It provided a good method for the synthesis of imidazoquinoline derivatives.

Key Words: imidazoquinoline  1H-benzo[d]imidazol-5-amine  region-selectivity  ring cyclopentane-1,3-dione  synthesis.

目  录

摘要--Ⅰ

Abstract-Ⅱ

目录--Ⅲ

表清单---Ⅳ

1 绪论-1

2本课题目前的研究状况与水平---2

2.1 实验内容-4

3 化合物表征---5

4 实验结果与讨论---11

4. 1 实验结果与讨论---11

4. 2 可能的反应机理---12

5 结论---14

参考文献15

致谢--17

表1. 反应时间和化合物4的产率

Entry Ar Time (h) Products Isolated yields (%)

1 benzo[d][1,3]dioxol-5-yl 8 4a 88

2 3,5-(MeO)2C6H3 7 4b 86

3 4-FC6H4 9 4c 88

4 3-MeOC6H4 10 4d 78

5 4-BrC6H4 8 4e 90

6 3-ClC6H4 6 4f 88

7 4-ClC6H4 10 4g 89

8 3,4-Cl2C6H3 9 4h 77

9 2-CH3OC6H4 7 4i 81

10 9-CNC6H4 5 4j  86

11 4-MeOC6H4