氮杂环卡宾催化合成吲哚并硫吡喃酮及吲哚并吡啶酮类化合物

发布时间：2018-03-01 14:14

本文关键词： 氮杂环卡宾 [3+3]环化反应吲哚并二氢硫吡喃酮吲哚并二氢吡啶酮 α-咔啉　出处：《山东大学》2017年硕士论文　论文类型：学位论文

【摘要】：近年来,氮杂环卡宾作为一种强有力的有机小分子催化剂在构建碳-碳键及碳-杂键方面得到了广泛的关注与深入的研究。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-吲哚亚胺类化合物为底物,分别与α-溴代烯醛在氮杂环卡宾催化作用下形成的α,β-不饱和酰基唑中间体反应,通过一锅法成功构建了碳-碳键、碳-硫键或碳-氮键。论文第一部分是氮杂环卡宾催化α-溴代烯醛形成的α,β-不饱和酰基唑中间体与2-吲哚硫酮发生的[3+3]环化反应,高效地合成出了吲哚并二氢硫吡喃酮类化合物。该类化合物是很多天然产物及药物的核心骨架结构。值得一提的是在氮杂环卡宾催化构建碳-杂键的研究中,绝大部分工作集中在碳-氮及碳-氧键的构建上,碳-硫键的构建鲜有报道。论文第二部分是氮杂环卡宾催化α-溴代烯醛形成的α,β-不饱和酰基唑中间体与2-吲哚亚胺发生的[3+3]环化反应,高效的合成出了吲哚并二氢吡啶酮类化合物。通过文献调研发现,该类化合物可以通过适当的合成转化策略,成功衍生出具有广泛生物活性的α-咔啉类化合物。相比于文献已报导的合成此类化合物的方法,该策略可合成出其已有方法所不能合成出的一些化合物,从而丰富了这类化合物的多样性,为日后研究着它的生物及药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 伪, 尾 -unsaturated acylazole intermediates with 伪 -bromoalkenal catalyzed by heterocyclic carbenes. Carbon-sulfur bond or carbon-nitrogen bond. The first part of this thesis is the [33] cyclization of 伪, 尾 -unsaturated acylazolium intermediates with 2-indole-thione catalyzed by 伪 -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 伪, 尾 -unsaturated acylazole intermediates with 2-indolimide catalyzed by 伪 -bromo-alkenal catalyzed by heterocyclic carbenes. The indole dihydropyridone compounds were synthesized efficiently. 伪 -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.
【学位授予单位】：山东大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O626

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