多组分反应构建含吲哚结构杂环化合物的研究
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摘要
吲哚类化合物是一类重要的杂环化合物,具有显著的生物活性和应用功能。含吲哚骨架化合物及其衍生物的合成以及性能研究,一直是广大学者的研究热点之一。多组分反应策略由于其连续、简便和高效的优点,特别是实现快速、大量地合成具有结构多样性和复杂性的化合物,用于优化和筛选具有药理活性苗头的前导化合物,越来越引起了化学和药物学工作者的极大兴趣。本论文主要研究了利用多组分反应方法,与微波和水相等多种反应手段相结合,设计合成多类具有多个活性部位的含吲哚结构的螺环和稠环杂环化合物。研究主要包括以下几方面内容:
第一部分通过傅克酰化反应,我们设计合成了含吲哚结构的活泼化合物氰乙酰基吲哚。以此为底物,采用多组分一锅法简便、高效地合成了双吲哚取代的3,5-二氰基吡啶和双吲哚取代的3,5-二氰基-1,4-二氢吡啶化合物。该类化合物结构新颖,具有较有意义的杂环骨架,我们对其相关的光学性质做了初步的表征。同时我们进一步合成了一系列非对称的双吲哚吡啶化合物,以及三吲哚、多吲哚取代吡啶杂环衍生物。
第二部分我们研究了氰乙酰基吲哚,醛和活泼氨基化合物的多组分反应。通过对反应底物的筛选,合成得到了多个系列的含吲哚结构的二元、三元含氮杂环化合物,实现了多个活性杂环骨架的联接和组合,方法简便实用,产物选择性较好,且底物适用范围较广。
第三部分我们发展了环境友好条件下合成羟吲哚螺环化合物的方法,即在水相条件下,以TEBAC为催化剂,一步实现靛红、活泼亚甲基化合物、活泼羰基化合物的三组分反应。该反应条件温和,产率较高,同时我们给出了可能的反应机理。
第四部分我们将微波技术和水相反应相结合,在无催化剂的条件下,三组分一锅法快速合成了一系列靛红螺苯并吡喃、靛红螺吡唑并吡喃和靛红螺吡喃并喹啉衍生物。实现了由廉价易得的原料,简便、快速、洁净地合成结构复杂的靛红螺环化合物,为该类化合物的研究提供了一条方便、有效的绿色合成方法。
第五部分我们在微波辐射条件下,以靛红、活泼亚甲基化合物和烯胺酮类化合物为原料,三组分反应合成了一系列靛红螺吡啶类杂环衍生物。反应时间较短,操作简便,得到的新的螺杂环化合物经过波谱分析表征及单晶X-衍射确证结构。
The indole nucleus is probably the most well-known heterocycle. Compounds carrying the indole moiety exhibit antibacterial and antifungal activities. Multicomponent reactions (MCRs) are of increasing importance in organic and medicinal chemistry. The strategies of MCRs offer significant advantages over conventional linear-type syntheses for their high degree of atom economy, convergence, ease of execution, and broad applications characters, which are particularly useful to generate diverse chemical libraries of‘druglike’molecules for biological screening. In this dissertation, much attention has been focused on the MCRs in the synthesis of indole-containing heterocycles. The whole work is mainly composed of following six parts:
Part I: A class of indole-containing activated compounds, 3-cyanoacetyl indoles prepared by the Friedel-Crafts acylation reactions, were employed to synthesize a series of 4-aryl-3,5-dicyano-2,6-di(3′-indolyl)pyridine and 4-aryl-3,5-dicyano-1,4-dihydro-2,6-di(3′-indolyl)pyridine derivatives via one-pot MCRs. The compounds were examined by UV-vis and fluorescence emission spectrum for their special structures and potential optical characterers. Moreover, a series of unsymmetric bis(3′-indolyl)pyridine, as well as tri(3′-indolyl)pyridine and multi indolyl-substituted pyridine derivatives were also obtained.
Part II: Series of new 3′-indolyl substituted heterocycles, with which 3′-indolyl group binding in position of the nitrogen-containing nucleus were synthesized via three-component reactions of aldehydes, 3-cyanoacetyl indoles with activated amino compounds under both classical oil bath heating and microwave irradiation (MWI) conditions. This protocol has the advantages of high yields of products, broad substrate scope and easy handling.
Part III: A simple and clean procedure for three-component synthesis of spirooxindoles catalysted by triethylbenzylammonium chloride (TEBAC) in aqueous medium is described. Particularly valuable features of this method include environmentally benign character, high yields processing and straightforward procedure. Plausible mechanism of the reaction is also presented.
Part IV: An efficicent methodology for the synthesis spirooxindoles under MWI in water without catalysts is developed. The current process provides a simple and green method to obtain a variety of novel spirooxindoles, which may have potential biological activities.
Part V: A facile microwave-assisted synthesis of new spiro[indoline-pyridine] derivatives by one-pot multicomponent reaction of isatins, activated methylene reagent and enaminones, is described. The products were characterized by spectral data and the structure was confirmed by X-ray crystallographic analysis.
第一部分通过傅克酰化反应,我们设计合成了含吲哚结构的活泼化合物氰乙酰基吲哚。以此为底物,采用多组分一锅法简便、高效地合成了双吲哚取代的3,5-二氰基吡啶和双吲哚取代的3,5-二氰基-1,4-二氢吡啶化合物。该类化合物结构新颖,具有较有意义的杂环骨架,我们对其相关的光学性质做了初步的表征。同时我们进一步合成了一系列非对称的双吲哚吡啶化合物,以及三吲哚、多吲哚取代吡啶杂环衍生物。
第二部分我们研究了氰乙酰基吲哚,醛和活泼氨基化合物的多组分反应。通过对反应底物的筛选,合成得到了多个系列的含吲哚结构的二元、三元含氮杂环化合物,实现了多个活性杂环骨架的联接和组合,方法简便实用,产物选择性较好,且底物适用范围较广。
第三部分我们发展了环境友好条件下合成羟吲哚螺环化合物的方法,即在水相条件下,以TEBAC为催化剂,一步实现靛红、活泼亚甲基化合物、活泼羰基化合物的三组分反应。该反应条件温和,产率较高,同时我们给出了可能的反应机理。
第四部分我们将微波技术和水相反应相结合,在无催化剂的条件下,三组分一锅法快速合成了一系列靛红螺苯并吡喃、靛红螺吡唑并吡喃和靛红螺吡喃并喹啉衍生物。实现了由廉价易得的原料,简便、快速、洁净地合成结构复杂的靛红螺环化合物,为该类化合物的研究提供了一条方便、有效的绿色合成方法。
第五部分我们在微波辐射条件下,以靛红、活泼亚甲基化合物和烯胺酮类化合物为原料,三组分反应合成了一系列靛红螺吡啶类杂环衍生物。反应时间较短,操作简便,得到的新的螺杂环化合物经过波谱分析表征及单晶X-衍射确证结构。
The indole nucleus is probably the most well-known heterocycle. Compounds carrying the indole moiety exhibit antibacterial and antifungal activities. Multicomponent reactions (MCRs) are of increasing importance in organic and medicinal chemistry. The strategies of MCRs offer significant advantages over conventional linear-type syntheses for their high degree of atom economy, convergence, ease of execution, and broad applications characters, which are particularly useful to generate diverse chemical libraries of‘druglike’molecules for biological screening. In this dissertation, much attention has been focused on the MCRs in the synthesis of indole-containing heterocycles. The whole work is mainly composed of following six parts:
Part I: A class of indole-containing activated compounds, 3-cyanoacetyl indoles prepared by the Friedel-Crafts acylation reactions, were employed to synthesize a series of 4-aryl-3,5-dicyano-2,6-di(3′-indolyl)pyridine and 4-aryl-3,5-dicyano-1,4-dihydro-2,6-di(3′-indolyl)pyridine derivatives via one-pot MCRs. The compounds were examined by UV-vis and fluorescence emission spectrum for their special structures and potential optical characterers. Moreover, a series of unsymmetric bis(3′-indolyl)pyridine, as well as tri(3′-indolyl)pyridine and multi indolyl-substituted pyridine derivatives were also obtained.
Part II: Series of new 3′-indolyl substituted heterocycles, with which 3′-indolyl group binding in position of the nitrogen-containing nucleus were synthesized via three-component reactions of aldehydes, 3-cyanoacetyl indoles with activated amino compounds under both classical oil bath heating and microwave irradiation (MWI) conditions. This protocol has the advantages of high yields of products, broad substrate scope and easy handling.
Part III: A simple and clean procedure for three-component synthesis of spirooxindoles catalysted by triethylbenzylammonium chloride (TEBAC) in aqueous medium is described. Particularly valuable features of this method include environmentally benign character, high yields processing and straightforward procedure. Plausible mechanism of the reaction is also presented.
Part IV: An efficicent methodology for the synthesis spirooxindoles under MWI in water without catalysts is developed. The current process provides a simple and green method to obtain a variety of novel spirooxindoles, which may have potential biological activities.
Part V: A facile microwave-assisted synthesis of new spiro[indoline-pyridine] derivatives by one-pot multicomponent reaction of isatins, activated methylene reagent and enaminones, is described. The products were characterized by spectral data and the structure was confirmed by X-ray crystallographic analysis.
引文
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