【摘要】：含吲哚骨架有機(jī)化合物是自然界中普遍存在的重要雜環(huán)化合物之一,由于具有廣泛的生物活性和藥理活性在醫(yī)藥和有機(jī)合成領(lǐng)域中有了越來越多的應(yīng)用。近年來,許多新型含吲哚骨架衍生物在研發(fā)新藥的過程中,發(fā)揮了重要的作用。因此,設(shè)計(jì)和合成結(jié)構(gòu)新穎的含有吲哚骨架雜環(huán)化合物是一項(xiàng)有意義的工作。本論文分為五部分:第一部分,在查閱了相關(guān)文獻(xiàn)的基礎(chǔ)上,對含碘代吲哚骨架的雜環(huán)化合物進(jìn)行綜述。第二部分,5-碘靛紅1與水合肼反應(yīng)得到5-碘-2-吲哚酮2;N,N-二甲基甲(乙)酰胺與三氯氧磷形成Vilsmeier試劑,再與化合物2反應(yīng),合成2-氯-5-碘-3-吲哚甲醛3a和2-氯-3-乙酰基-5-碘吲哚3b;分別對化合物3a,3b烴基化,得到1-烴基-2-氯-5-碘-3-吲哚甲醛4a~4e和1-烴基-2-氯-3-乙�；�-5-碘吲哚4f~4j;以4a~4j為底物和硝酸胍在氫氧化鉀堿性條件下縮合,以40-65%的收率得到了9H-吲哚[4,5-b]并嘧啶-2-胺類衍生物5a~5j。第三部分,以5-(甲/乙/叔丁)基靛紅和7-(甲/乙)基靛紅為底物,碘代得到5-(甲/乙/叔丁)基-7-碘靛紅6~8和7-(甲/乙)基-5-碘靛紅9,10;再以1和6~10為原料,經(jīng)氮上烴基化得到1-烴基-5-碘靛紅1a~1e、1-烴基-5-(甲/乙/叔丁)基-7-碘靛紅6a~6e,7a~7e,8a~8e和1-烴基-7-(甲/乙)基-5-碘靛紅9a~9e,10a~10e;化合物1a~1e,6a~6e,7a~7e,8a~8e,9a~9e,10a~10e再與鄰苯二胺在冰醋酸為溶劑條件下回流反應(yīng),以78-88%的收率合成了6H-吲哚[2,3-b]并喹喔啉類衍生物11aa~11bd。第四部分,以1-烴基-5-碘靛紅1a~1e、1-烴基-5-(甲/乙/叔丁)基-7-碘靛紅6a~6e,7a~7e,8a~8e為底物與硫代氨基脲在以二氧六環(huán)為溶劑、碳酸鉀堿性條件下回流反應(yīng),合成了5H-[1,2,4]三嗪[5,6-b]并吲哚-3-硫醇類化合物12a~12t。第五部分,以1-甲基-2-氯-3-乙�；�-5-碘吲哚4f為原料與靛紅衍生物在10%乙醇-水為溶劑、氫氧化鉀堿性條件下,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均為新化合物,并利用紅外光譜、核磁共振氫譜和碳譜以及高分辨質(zhì)譜對其結(jié)構(gòu)進(jìn)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，

本文編號：2473563