基于2-氨基喹啉的新型喹啉并嘧啶类化合物的合成研究
发布时间：2019-06-20 12:40
【摘要】：喹啉并嘧啶类衍生物作为一类非常重要的杂环化合物,广泛存在于天然产物中并表现出良好的生物、药理活性,这类化合物主要被应用于杀虫剂、抗菌消炎药剂、及抗癌药物等方面。本论文以2-氨基喹啉为研究对象,针对杂环修饰的喹啉类衍生物的合成方法开展工作,具体工作如下:第一部分,通过查阅大量的相关文献,对喹啉并嘧啶类衍生物的合成路径、药理活性、应用研究进行了综述。第二部分,以2-氨基喹啉-3-甲酸乙酯为反应底物,无需催化剂,在乙醇为溶剂条件下,与DMFDMA和伯胺一锅法反应,高选择性地制备了嘧啶并[4,5-b]喹啉-4(3H)-酮类化合物。第三部分,以2-氨基-3-氰基喹啉为基本原料,在氢氧化钠作用下,通过2-氨基-3-氰基喹啉与醛类的缩合反应,合成2,3-二氢嘧啶并[4,5-b]喹啉-4(1H)-酮类衍生物。第四部分,以2-氨基-3-氰基喹啉为反应原料,在微波作用下,通过2-氨基-3-氰基喹啉与DMFDMA、伯胺一锅法反应,合成嘧啶并[4,5-b]喹啉-4-胺类衍生物。合成的所有化合物结构均经过红外、核磁共振、元素分析等手段进行了表征。
[Abstract]:Quinolacil derivatives, as a kind of very important heterocycle compounds, widely exist in natural products and show good biological and pharmacological activity. these compounds are mainly used in pesticides, antibacterial and anti-inflammatory agents, and anticancer drugs and so on. In this paper, 2-aminoquinoline was taken as the research object, and the synthesis methods of heterocycle modified quinolines were carried out as follows: in the first part, the synthesis path, pharmacological activity and application of quinolinopyrimidine derivatives were reviewed by consulting a large number of related literatures. In the second part, pyrimidine [4, 5 脳 b] quinolin-4 (3 H)-ketone compounds were prepared by one-pot reaction with DMFDMA and primary amine with 2-aminoquinolin-3-formate as substrate without catalyst and ethanol as solvent. In the third part, 2, 3-dihydropyrimido [4, 5 脳 b] quinolin-4 (1H)-ketone derivatives were synthesized by condensation of 2-amino-3-cyanoquinoline with aldehydes under the action of sodium hydroxide. In the fourth part, pyrimidine [4, 5 脳 b] quinoline-4-amine derivatives were synthesized by the one-pot reaction of 2-amino-3-cyanoquinoline with DMFDMA, primary amine under microwave irradiation. The structures of all the synthesized compounds were characterized by IR, NMR and elemental analysis.
【学位授予单位】：渤海大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O626
本文编号：2503226
[Abstract]:Quinolacil derivatives, as a kind of very important heterocycle compounds, widely exist in natural products and show good biological and pharmacological activity. these compounds are mainly used in pesticides, antibacterial and anti-inflammatory agents, and anticancer drugs and so on. In this paper, 2-aminoquinoline was taken as the research object, and the synthesis methods of heterocycle modified quinolines were carried out as follows: in the first part, the synthesis path, pharmacological activity and application of quinolinopyrimidine derivatives were reviewed by consulting a large number of related literatures. In the second part, pyrimidine [4, 5 脳 b] quinolin-4 (3 H)-ketone compounds were prepared by one-pot reaction with DMFDMA and primary amine with 2-aminoquinolin-3-formate as substrate without catalyst and ethanol as solvent. In the third part, 2, 3-dihydropyrimido [4, 5 脳 b] quinolin-4 (1H)-ketone derivatives were synthesized by condensation of 2-amino-3-cyanoquinoline with aldehydes under the action of sodium hydroxide. In the fourth part, pyrimidine [4, 5 脳 b] quinoline-4-amine derivatives were synthesized by the one-pot reaction of 2-amino-3-cyanoquinoline with DMFDMA, primary amine under microwave irradiation. The structures of all the synthesized compounds were characterized by IR, NMR and elemental analysis.
【学位授予单位】：渤海大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O626
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