基于2-氨基喹啉的新型喹啉并嘧啶類化合物的合成研究
發(fā)布時間：2019-06-20 12:40
【摘要】：喹啉并嘧啶類衍生物作為一類非常重要的雜環(huán)化合物,廣泛存在于天然產(chǎn)物中并表現(xiàn)出良好的生物、藥理活性,這類化合物主要被應用于殺蟲劑、抗菌消炎藥劑、及抗癌藥物等方面。本論文以2-氨基喹啉為研究對象,針對雜環(huán)修飾的喹啉類衍生物的合成方法開展工作,具體工作如下:第一部分,通過查閱大量的相關(guān)文獻,對喹啉并嘧啶類衍生物的合成路徑、藥理活性、應用研究進行了綜述。第二部分,以2-氨基喹啉-3-甲酸乙酯為反應底物,無需催化劑,在乙醇為溶劑條件下,與DMFDMA和伯胺一鍋法反應,高選擇性地制備了嘧啶并[4,5-b]喹啉-4(3H)-酮類化合物。第三部分,以2-氨基-3-氰基喹啉為基本原料,在氫氧化鈉作用下,通過2-氨基-3-氰基喹啉與醛類的縮合反應,合成2,3-二氫嘧啶并[4,5-b]喹啉-4(1H)-酮類衍生物。第四部分,以2-氨基-3-氰基喹啉為反應原料,在微波作用下,通過2-氨基-3-氰基喹啉與DMFDMA、伯胺一鍋法反應,合成嘧啶并[4,5-b]喹啉-4-胺類衍生物。合成的所有化合物結(jié)構(gòu)均經(jīng)過紅外、核磁共振、元素分析等手段進行了表征。
[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.
【學位授予單位】：渤海大學
【學位級別】：碩士
【學位授予年份】：2017
【分類號】：O626
本文編號：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.
【學位授予單位】：渤海大學
【學位級別】：碩士
【學位授予年份】：2017
【分類號】：O626
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