【摘要】：由于C-H鍵直接官能團化反應與傳統(tǒng)方法相比具有高效、原子經(jīng)濟性、步驟簡單、成本低廉等優(yōu)勢,近年來得到化學家的廣泛關(guān)注,并成功地應用于藥物分子、天然產(chǎn)物和功能材料的合成。大多數(shù)有機分子含有多個C-H鍵,選擇性地對特定位置上C-H鍵進行官能團轉(zhuǎn)化,合成高附加值的目標產(chǎn)物是該領域的一個棘手問題,化學家通過在底物中引入誘導基成功地解決了該問題。此外,雜環(huán)化合物中雜原子的存在使得分子中C-H鍵活性存在明顯差異,無需導向基團既可以實現(xiàn)特定位置的區(qū)域官能團化,利用這一性質(zhì),科學家們實現(xiàn)了大量的雜環(huán)化合物的區(qū)域選擇性官能團化反應。另外,吲哚廣泛地存在于生物活性分子和天然產(chǎn)物中,并且是重要的有機合成中間體,因此關(guān)于吲哚衍生物的合成方法研究一直是有機化學家研究的熱點之一。本論文主要研究了通過多分子串聯(lián)反應,以簡單吲哚、醛和醇為底物,堿促進一鍋法合成3-烷氧基甲基吲哚衍生物(Scheme 1)。該方法高效、快捷、成本低廉、原料易得,并且無需添加過渡金屬及其他的添加劑。依據(jù)實驗結(jié)果及相關(guān)文獻報道,推測反應機理如下(Scheme 2):
[Abstract]:Because C-H bond direct functional reaction has the advantages of high efficiency, atomic economy, simple steps and low cost compared with traditional methods, it has been widely concerned by chemists in recent years, and has been successfully applied to drug molecules. Synthesis of natural products and functional materials. Most organic molecules contain multiple C-H bonds. The selective conversion of C-H bonds to specific sites and the synthesis of target products with high added value are a thorny problem in this field. Chemists successfully solved the problem by introducing inducers into the substrate. In addition, the presence of hetero atoms in heterocyclic compounds makes the C-H bond activity in the molecule significantly different. Scientists have achieved a large number of heterocyclic compounds of regioselective functional reactions. In addition, indole widely exists in bioactive molecules and natural products, and is an important intermediate of organic synthesis. Therefore, the research on the synthetic methods of indole derivatives has been one of the hot spots of organic chemists. In this paper, the synthesis of 3-alkoxy methyl indole derivative (Scheme _ 1) in one pot with simple indole, aldehyde and alcohol in series reaction was studied. The method is efficient, fast, low cost, easy to obtain raw materials and does not need to add transition metal and other additives. According to the experimental results and related literature reports, the mechanism of the reaction is as follows (Scheme 2):
【學位授予單位】：鄭州大學
【學位級別】：碩士
【學位授予年份】：2017
【分類號】：O626

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本文編號：2210031