發(fā)布時(shí)間：2018-04-24 15:58

  本文選題：7-乙基吲哚-2-酮 + Claisen-Schmidt縮合反應(yīng)　； 參考：《渤海大學(xué)》2017年碩士論文

【摘要】：含有吲哚環(huán)的化合物是自然界里的最常見(jiàn)的雜環(huán)化合物之一,由于該類(lèi)化合物具有獨(dú)特的化學(xué)結(jié)構(gòu)、良好的生物活性及特殊的藥理活性,所以該類(lèi)化合物能夠廣泛地應(yīng)用于工業(yè)、香料、醫(yī)藥、農(nóng)藥、飼料以及有機(jī)中間體合成等方面。因此,探究含有吲哚骨架的新型雜環(huán)化合物的合成具有重要的意義。本論文主要分為五部分。第一部分,經(jīng)過(guò)查閱關(guān)于吲哚及其衍生物的文獻(xiàn),對(duì)含吲哚環(huán)類(lèi)化合物的合成、性質(zhì)、應(yīng)用和近年來(lái)的研究狀況進(jìn)行綜述。第二部分,以7-乙基靛紅(1)為原料與水合肼發(fā)生還原反應(yīng),得到了7-乙基吲哚-2-酮(2);化合物(2)在哌啶為堿、乙醇為溶劑的條件下,與芳醛(3a-3t)發(fā)生了Claisen-Schmidt縮合反應(yīng),進(jìn)而得到(Z)-3-亞芐基-7-乙基吲哚-2-酮類(lèi)化合物(4a-4t)。第三部分,以7-乙基吲哚-2-酮(2)為原料與氯乙酰氯發(fā)生酰化反應(yīng),得到5-氯乙�；�-7-乙基吲哚-2-酮(5);然后以化合物(5)為底物與取代硫脲及硫代酰胺發(fā)生Handzseh反應(yīng),得到7-乙基-5-(2-烴基噻唑-5-基)吲哚-2-酮(6a-6v)。第四部分,以7-乙基吲哚-2-酮(2)為底物與Vilsmeier-Haack試劑反應(yīng),得到2-氯-7-乙基-3-甲醛(乙酰)吲哚(7a,7b);將化合物(7a,7b)進(jìn)行N上烴基化,得到N-烴基-2-氯-7-乙基-3-甲醛(乙酰)吲哚(8a-8j);以化合物(8a-8j)為底物、乙醇為溶劑,與鹽酸羥氨作用得N-烴基-7-乙基-2-氯-吲哚-3-酮肟(9a-9j)。第五部分,以7-乙基靛紅(1)為起始原料烴基化,得到1-烴基-7-乙基靛紅(10a-10e);化合物(10a-10e)經(jīng)水合肼還原得到N-烴基-7-乙基吲哚-2-酮(11a-11e);以化合物(11a-11e)為底物,在乙酸酐及4-二甲氨基吡啶(DMAP)作用下得到2、3位酰基化的中間體,然后以四氫呋喃為溶劑、5%氫氧化鈉為堿的條件下水解,得到3-乙�；�-1-烴基-2-羥基-7-乙基-吲哚(12a-12e)。本論文新合成的化合物結(jié)構(gòu)都經(jīng)過(guò)紅外光譜,核磁共振氫譜、碳譜、高分辨質(zhì)譜表征。
[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.
【學(xué)位授予單位】：渤海大學(xué)
【學(xué)位級(jí)別】：碩士
【學(xué)位授予年份】：2017
【分類(lèi)號(hào)】：O626

【參考文獻(xiàn)】

相關(guān)期刊論文 前10條

1 趙雅楠;符鑫博;李陽(yáng);王東方;高文濤;;7-乙基-2-吲哚酮與芳醛的Claisen-Schmidt縮合反應(yīng)研究[J];化學(xué)研究與應(yīng)用;2016年10期

2 高文濤;白仁青卓瑪;蘭帥;李凱;;5-乙基-2-吲哚酮的合成及其�；蚇上烴基化反應(yīng)研究[J];化學(xué)研究與應(yīng)用;2015年02期

3 高文濤;蘭帥;鄭宏梅;白仁青卓瑪;;含噻唑骨架的吲哚衍生物的有效合成[J];有機(jī)化學(xué);2015年01期

4 鐘霞;安平;張俊清;黃劍;陳年根;;吲哚醌類(lèi)Schiff堿及其配合物的合成與抗腫瘤活性研究[J];化學(xué)研究與應(yīng)用;2012年07期

5 陸國(guó)秀;張彩霞;辛軍;刁堯;高繼東;;~(131)碘-組胺-吲哚美辛對(duì)小鼠荷Lewis肺癌的治療效果及其作用機(jī)制的研究[J];現(xiàn)代腫瘤醫(yī)學(xué);2012年06期

6 唐嘯威;謝文利;陳虹;田丹麗;左松;白淑芳;;吲哚草酰類(lèi)鬼臼毒素衍生物的合成及其抗腫瘤活性[J];天津醫(yī)科大學(xué)學(xué)報(bào);2011年03期

7 魏金建;王艷;王憲龍;周成合;吉慶剛;;1,2,3-三唑類(lèi)化合物在醫(yī)藥領(lǐng)域的研究新進(jìn)展[J];中國(guó)藥學(xué)雜志;2011年07期

8 Dhanaji V.Jawale;Dinesh L.Lingampalle;Umesh R.Pratap;Ramrao A.Mane;;One-pot synthesis of 2-aminothiazoles in PEG-400[J];Chinese Chemical Letters;2010年04期

9 黃以鐘;潘大仁;周以飛;;含吲哚苷植物在福建的資源及分布[J];海峽藥學(xué);2010年02期

10 呂文輝;劉興海;劉冬妍;石雷;孫琪;;鐵、鈷或鎳助劑促進(jìn)的Ag/SiO_2催化劑上氣相催化合成3-甲基吲哚[J];催化學(xué)報(bào);2009年12期

，

本文編號(hào)：1797296