基于7-乙基吲哚-2-酮杂环化合物的合成与表征

发布时间：2018-04-24 15:58

本文选题：7-乙基吲哚-2-酮 + Claisen-Schmidt缩合反应　；参考：《渤海大学》2017年硕士论文

【摘要】：含有吲哚环的化合物是自然界里的最常见的杂环化合物之一,由于该类化合物具有独特的化学结构、良好的生物活性及特殊的药理活性,所以该类化合物能够广泛地应用于工业、香料、医药、农药、饲料以及有机中间体合成等方面。因此,探究含有吲哚骨架的新型杂环化合物的合成具有重要的意义。本论文主要分为五部分。第一部分,经过查阅关于吲哚及其衍生物的文献,对含吲哚环类化合物的合成、性质、应用和近年来的研究状况进行综述。第二部分,以7-乙基靛红(1)为原料与水合肼发生还原反应,得到了7-乙基吲哚-2-酮(2);化合物(2)在哌啶为碱、乙醇为溶剂的条件下,与芳醛(3a-3t)发生了Claisen-Schmidt缩合反应,进而得到(Z)-3-亚苄基-7-乙基吲哚-2-酮类化合物(4a-4t)。第三部分,以7-乙基吲哚-2-酮(2)为原料与氯乙酰氯发生酰化反应,得到5-氯乙酰基-7-乙基吲哚-2-酮(5);然后以化合物(5)为底物与取代硫脲及硫代酰胺发生Handzseh反应,得到7-乙基-5-(2-烃基噻唑-5-基)吲哚-2-酮(6a-6v)。第四部分,以7-乙基吲哚-2-酮(2)为底物与Vilsmeier-Haack试剂反应,得到2-氯-7-乙基-3-甲醛(乙酰)吲哚(7a,7b);将化合物(7a,7b)进行N上烃基化,得到N-烃基-2-氯-7-乙基-3-甲醛(乙酰)吲哚(8a-8j);以化合物(8a-8j)为底物、乙醇为溶剂,与盐酸羟氨作用得N-烃基-7-乙基-2-氯-吲哚-3-酮肟(9a-9j)。第五部分,以7-乙基靛红(1)为起始原料烃基化,得到1-烃基-7-乙基靛红(10a-10e);化合物(10a-10e)经水合肼还原得到N-烃基-7-乙基吲哚-2-酮(11a-11e);以化合物(11a-11e)为底物,在乙酸酐及4-二甲氨基吡啶(DMAP)作用下得到2、3位酰基化的中间体,然后以四氢呋喃为溶剂、5%氢氧化钠为碱的条件下水解,得到3-乙酰基-1-烃基-2-羟基-7-乙基-吲哚(12a-12e)。本论文新合成的化合物结构都经过红外光谱,核磁共振氢谱、碳谱、高分辨质谱表征。
[Abstract]:Compounds containing indole ring are one of the most common heterocyclic compounds in nature because of their unique chemical structure, good biological activity and special pharmacological activity. Therefore, these compounds can be widely used in industry, spices, medicine, pesticides, feed and organic intermediates synthesis. Therefore, it is of great significance to explore the synthesis of new heterocyclic compounds containing indole skeleton. This paper is divided into five parts. In the first part, the synthesis, properties, applications and recent studies of indole and its derivatives were reviewed. In the second part, 7-ethylindophenone 1) was reduced to hydrazine hydrate to obtain 7-ethylindole -2-ketonone 2n; compound 2) was condensed with aromatic aldehydes (3a-3t) under the condition of piperidine as base and ethanol as solvent. Furthermore, a 4a-4the compound of Zhe-3-benzylidene-7-ethyl indole-2-ketone was obtained. In the third part, 5-Chloroacetyl-7-ethyl-indole -2-ketonone 2) was acylated with chloroacetyl chloride and then reacted with substituted thiourea and thioamide using compound 5) as substrate. 7-ethyl -5-butadiene-2-alkylthiazole-5-yl) indole-2-ketone 6a-6vn was obtained. In the fourth part, 2-chloro-7-ethyl-3-formaldehyde (acetyl) indole-3-formaldehyde (acetyl) indole-3-formaldehyde (acetyl) -3-formaldehyde (acetyl) indole-3-formaldehyde (acetyl) was synthesized by the reaction of 7-ethylindole -2-keto-2) with Vilsmeier-Haack reagent. N- alkyl-2-chloro-7-ethyl-3-formaldehyde (acetyl) indole 8a-8jn was synthesized by the reaction of ethanol with hydroxy ammonia hydrochloride to give N- alkyl-7-ethyl-2-chloro-indole-3-ketone oxime 9a-9joxime. Part V, using 7ethylindirubin 1) as the starting material, the alkylation of 1-alkyl-7-ethylindirubin 10a-10en; the compound 10a-10e) is reduced by hydrazine hydrate to obtain N-alkyl-7-ethyl-indole -2-ketonone 11a-11en; and the compound 11a-11e is used as the substrate, In the presence of acetic anhydride and 4-dimethylaminopyridine dimethylpyridine (DMAP), the intermediate at 2o 3 was obtained, and then hydrolyzed with tetrahydrofuran as solvent 5% sodium hydroxide as base to obtain 3acetyl-1-alkyl-2-hydroxy-7ethyl-indole 12a-12e. In this paper, the structures of the new compounds were characterized by IR, NMR, carbon and high resolution mass spectrometry.
【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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