含碘代吲哚骨架的杂环化合物的合成与表征
发布时间：2019-05-10 10:06
【摘要】：含吲哚骨架有机化合物是自然界中普遍存在的重要杂环化合物之一,由于具有广泛的生物活性和药理活性在医药和有机合成领域中有了越来越多的应用。近年来,许多新型含吲哚骨架衍生物在研发新药的过程中,发挥了重要的作用。因此,设计和合成结构新颖的含有吲哚骨架杂环化合物是一项有意义的工作。本论文分为五部分:第一部分,在查阅了相关文献的基础上,对含碘代吲哚骨架的杂环化合物进行综述。第二部分,5-碘靛红1与水合肼反应得到5-碘-2-吲哚酮2;N,N-二甲基甲(乙)酰胺与三氯氧磷形成Vilsmeier试剂,再与化合物2反应,合成2-氯-5-碘-3-吲哚甲醛3a和2-氯-3-乙酰基-5-碘吲哚3b;分别对化合物3a,3b烃基化,得到1-烃基-2-氯-5-碘-3-吲哚甲醛4a~4e和1-烃基-2-氯-3-乙酰基-5-碘吲哚4f~4j;以4a~4j为底物和硝酸胍在氢氧化钾碱性条件下缩合,以40-65%的收率得到了9H-吲哚[4,5-b]并嘧啶-2-胺类衍生物5a~5j。第三部分,以5-(甲/乙/叔丁)基靛红和7-(甲/乙)基靛红为底物,碘代得到5-(甲/乙/叔丁)基-7-碘靛红6~8和7-(甲/乙)基-5-碘靛红9,10;再以1和6~10为原料,经氮上烃基化得到1-烃基-5-碘靛红1a~1e、1-烃基-5-(甲/乙/叔丁)基-7-碘靛红6a~6e,7a~7e,8a~8e和1-烃基-7-(甲/乙)基-5-碘靛红9a~9e,10a~10e;化合物1a~1e,6a~6e,7a~7e,8a~8e,9a~9e,10a~10e再与邻苯二胺在冰醋酸为溶剂条件下回流反应,以78-88%的收率合成了6H-吲哚[2,3-b]并喹喔啉类衍生物11aa~11bd。第四部分,以1-烃基-5-碘靛红1a~1e、1-烃基-5-(甲/乙/叔丁)基-7-碘靛红6a~6e,7a~7e,8a~8e为底物与硫代氨基脲在以二氧六环为溶剂、碳酸钾碱性条件下回流反应,合成了5H-[1,2,4]三嗪[5,6-b]并吲哚-3-硫醇类化合物12a~12t。第五部分,以1-甲基-2-氯-3-乙酰基-5-碘吲哚4f为原料与靛红衍生物在10%乙醇-水为溶剂、氢氧化钾碱性条件下,合成一系列9-碘-6-甲基-6H-吲哚[2,3-b]并喹啉-11-羧酸衍生物13a~13i。本文所合成的化合物5a~5j,11aa~11bd,12a~12t,13a~13i均为新化合物,并利用红外光谱、核磁共振氢谱和碳谱以及高分辨质谱对其结构进行了表征。
[Abstract]:Indole-containing organic compounds are one of the most important heterocycle compounds in nature. Because of their extensive biological and pharmacological activities, they have been widely used in the field of medicine and organic synthesis. In recent years, many new indole-containing skeleton derivatives have played an important role in the development of new drugs. Therefore, it is a meaningful work to design and synthesize novel heterocycle compounds containing indole skeleton. This paper is divided into five parts: in the first part, on the basis of consulting the relevant literature, the heterocycle compounds containing iodine indole skeleton are reviewed. In the second part, 5-iodine-2-indolone 2 was obtained by the reaction of 5-iodine indigo 1 with hydrazide hydrate. N, N-dimethyl A (ethyl) amide and phosphorus oxychloride form Vilsmeier reagent, and then react with compound 2 to synthesize 2-chloro-5-iodine-3-indole formaldehyde 3a and 2-chloro-3-acetyl5-iodoindole 3b. 1-alkyl-2-chloro-5-iodine-3-indole formaldehyde 4a~4e and 1-alkyl-2-chloro-3-acetyl5-iodoindole 4F 鈮，
本文编号：2473563
[Abstract]:Indole-containing organic compounds are one of the most important heterocycle compounds in nature. Because of their extensive biological and pharmacological activities, they have been widely used in the field of medicine and organic synthesis. In recent years, many new indole-containing skeleton derivatives have played an important role in the development of new drugs. Therefore, it is a meaningful work to design and synthesize novel heterocycle compounds containing indole skeleton. This paper is divided into five parts: in the first part, on the basis of consulting the relevant literature, the heterocycle compounds containing iodine indole skeleton are reviewed. In the second part, 5-iodine-2-indolone 2 was obtained by the reaction of 5-iodine indigo 1 with hydrazide hydrate. N, N-dimethyl A (ethyl) amide and phosphorus oxychloride form Vilsmeier reagent, and then react with compound 2 to synthesize 2-chloro-5-iodine-3-indole formaldehyde 3a and 2-chloro-3-acetyl5-iodoindole 3b. 1-alkyl-2-chloro-5-iodine-3-indole formaldehyde 4a~4e and 1-alkyl-2-chloro-3-acetyl5-iodoindole 4F 鈮，
本文编号：2473563
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