本文關(guān)鍵詞： 氮雜環(huán)卡賓 [3+3]環(huán)化反應(yīng) 吲哚并二氫硫吡喃酮 吲哚并二氫吡啶酮 α-咔啉　出處：《山東大學(xué)》2017年碩士論文　論文類型：學(xué)位論文

【摘要】：近年來,氮雜環(huán)卡賓作為一種強(qiáng)有力的有機(jī)小分子催化劑在構(gòu)建碳-碳鍵及碳-雜鍵方面得到了廣泛的關(guān)注與深入的研究。本文主要研究了基于以吲哚骨架衍生出的2-吲哚硫酮及2-吲哚亞胺類化合物為底物,分別與α-溴代烯醛在氮雜環(huán)卡賓催化作用下形成的α,β-不飽和�；蛑虚g體反應(yīng),通過一鍋法成功構(gòu)建了碳-碳鍵、碳-硫鍵或碳-氮鍵。論文第一部分是氮雜環(huán)卡賓催化α-溴代烯醛形成的α,β-不飽和�；蛑虚g體與2-吲哚硫酮發(fā)生的[3+3]環(huán)化反應(yīng),高效地合成出了吲哚并二氫硫吡喃酮類化合物。該類化合物是很多天然產(chǎn)物及藥物的核心骨架結(jié)構(gòu)。值得一提的是在氮雜環(huán)卡賓催化構(gòu)建碳-雜鍵的研究中,絕大部分工作集中在碳-氮及碳-氧鍵的構(gòu)建上,碳-硫鍵的構(gòu)建鮮有報(bào)道。論文第二部分是氮雜環(huán)卡賓催化α-溴代烯醛形成的α,β-不飽和�；蛑虚g體與2-吲哚亞胺發(fā)生的[3+3]環(huán)化反應(yīng),高效的合成出了吲哚并二氫吡啶酮類化合物。通過文獻(xiàn)調(diào)研發(fā)現(xiàn),該類化合物可以通過適當(dāng)?shù)暮铣赊D(zhuǎn)化策略,成功衍生出具有廣泛生物活性的α-咔啉類化合物。相比于文獻(xiàn)已報(bào)導(dǎo)的合成此類化合物的方法,該策略可合成出其已有方法所不能合成出的一些化合物,從而豐富了這類化合物的多樣性,為日后研究著它的生物及藥理活性提供了合成保障。
[Abstract]:In recent years, Nitrogen heterocyclic carbene as a powerful organic small molecule catalyst has been widely studied in the construction of carbon-carbon bond and carbon-heterogeneity bond. Indole thione and 2-indoleimide as substrates, The carbon-carbon bonds were successfully constructed by one-pot reaction of 偽, 尾 -unsaturated acylazole intermediates with 偽 -bromoalkenal catalyzed by heterocyclic carbenes. Carbon-sulfur bond or carbon-nitrogen bond. The first part of this thesis is the [33] cyclization of 偽, 尾 -unsaturated acylazolium intermediates with 2-indole-thione catalyzed by 偽 -bromo-alkenal. Indole dihydrothiopyranone compounds have been synthesized efficiently. These compounds are the core skeleton structures of many natural products and drugs. Most of the work focused on the construction of carbon-nitrogen and carbon-oxygen bonds. There are few reports on the construction of carbon-sulfur bonds. The second part is the [33] cyclization of 偽, 尾 -unsaturated acylazole intermediates with 2-indolimide catalyzed by 偽 -bromo-alkenal catalyzed by heterocyclic carbenes. The indole dihydropyridone compounds were synthesized efficiently. 偽 -carboline compounds with a wide range of biological activities have been successfully derived. Compared with the methods reported in the literature for the synthesis of such compounds, this strategy can synthesize some compounds which cannot be synthesized by their existing methods. It enriches the diversity of these compounds and provides a synthetic guarantee for the future study of their biological and pharmacological activities.
【學(xué)位授予單位】：山東大學(xué)
【學(xué)位級(jí)別】：碩士
【學(xué)位授予年份】：2017
【分類號(hào)】：O626

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1 蔣錫夔;;卡賓的化學(xué)[J];化學(xué)通報(bào);1962年07期

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4 馬艷鳳,馬楠,孟繁友;關(guān)于卡賓的研究[J];松遼學(xué)刊(自然科學(xué)版);1997年03期

5 孫小宇;吳R，

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