【摘要】：自從Passarini反應(yīng)和Ugi反應(yīng)被報(bào)道之后，異腈的親核性和親電性在多組分反應(yīng)(MCRs)中得到廣泛應(yīng)用。近十年來，異腈在過渡金屬催化反應(yīng)中作為萬能的C1建筑模塊代替CO的插入反應(yīng)得到了更多的關(guān)注。目前，，已有大量文獻(xiàn)報(bào)道了異腈插入反應(yīng)，主要集中在氮、氧親核試劑的羰基或亞胺酰基化。因此，本論文主要報(bào)道了過渡金屬催化異腈插入和碳、氮親核試劑偶聯(lián)建立C-C、C-N鍵的反應(yīng)，包括兩部分： 第一部分（第二章）是炔酮的合成，通過鈀催化的羰基化Sonogashira反應(yīng)，經(jīng)叔丁基異腈插入合成炔亞胺中間體，再經(jīng)簡單水解得到炔酮類化合物，實(shí)現(xiàn)了異腈插入反應(yīng)構(gòu)建分子間C-C鍵的目的。 第二部分（第三章、第四章）是含氮雜環(huán)類化合物的合成，包括鈀催化異腈插入和酸水解合成異吲哚并吲哚酮和茚并吲哚酮類化合物及鎳催化異腈插入不經(jīng)水解合成苯并咪唑并異吲哚亞胺衍生物。前者成功地通過異腈插入反應(yīng)構(gòu)建了分子內(nèi)的C-N、C-C鍵。后者再一次印證了鎳催化劑在異腈插入反應(yīng)中的高活性，得到的苯并咪唑并異吲哚亞胺衍生物的抗腫瘤活性正在研究之中。
[Abstract]:Since the Passarini reaction and Ugi reaction have been reported, the nucleophilic and electrophilic properties of isonitrile have been widely used in multicomponent reaction (MCRs). In recent ten years, more attention has been paid to the insertion of isonitrile as a universal C1 building module instead of CO in transition metal-catalyzed reactions. At present, a large number of literatures have reported the insertion reaction of isonitrile, mainly concentrated in nitrogen, oxygen nucleophilic reagent carbonyl or imide. Therefore, the transition metal catalyzed isonitrile insertion and the coupling of carbon and nitrogen nucleophilic reagents to form C-CN bond are reported in this paper, including two parts: the first part (chapter 2) is the synthesis of acetylene ketones. Through palladium catalyzed carbonylation Sonogashira reaction, the intermediate of acetyleimide was synthesized by insertion of tert-Ding Ji isonitrile, and then the alkyne ketones were simply hydrolyzed. The purpose of isonitrile insertion reaction to construct intermolecular C-C bond was achieved. The second part (Chapter III, Chapter IV) is the synthesis of nitrogen-containing heterocyclic compounds, It includes palladium catalyzed isonitrile insertion and acid hydrolysis synthesis of isoindole indole ketones and nickel catalyzed isonitrile insertion without hydrolysis to synthesize benzimidazole isoindolimide derivatives. The former has successfully constructed the intramolecular C-NN-C-C bond through the isonitrile insertion reaction. The latter confirmed the high activity of nickel catalyst in the isonitrile insertion reaction, and the antitumor activity of benzimidazole and isoindolimide derivatives was being studied.
【學(xué)位授予單位】：蘇州大學(xué)
【學(xué)位級別】：碩士
【學(xué)位授予年份】：2014
【分類號】：R914.5

【參考文獻(xiàn)】

相關(guān)期刊論文 前1條

1 劉學(xué)巍;甘海峰;錢祥均;鄒寶華;仲蕙;郭凱;;異腈參與的多組分反應(yīng)研究進(jìn)展[J];化學(xué)通報(bào);2013年02期

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