1，2，3-三唑的合成及钯催化的羰基化偶联反应研究
摘要
本论文共分为四章。
第一章对1，2，3-三唑的合成方法进行了介绍。1，2，3-三唑因为其独特的化学特性和结构，已经引起了广泛重视。目前为止，我们还没有从天然产物中分离到含1，2，3-三唑环结构的化合物。本文对不同的合成方式进行了总结，其中以Huisgen首先提出的叠氮化物与炔的1，3-偶极环加成反应最为重要。近年，Sharpless，Fokin等发展了Cu(I)催化的环加成合成1，2，3-三唑的反应。
第二章研究了在1，4-二氧六环和水的混合溶剂中CuI／CuSO_4催化的末端炔、苯基硼酸和叠氮钠的1，3-偶极环加成偶联反应，合成了一系列1，4，5-三取代的1，2，3-三唑。本章介绍了一种新颖的从苯基硼酸，叠氮钠及部分的末端炔合成1，4，5-三取代的1，2，3-三唑的方法，从而很好的避免了制备和分离有机叠氮的操作，因此这一方法显示了许多的优点，如安全、有效、操作方便、环境友好等。
第三章设计并合成了一类潜在的治疗老年痴呆症(AD)的化合物。AD已经成为威胁老年人生活质量和生命的主要疾病之一。在细胞水平上，AD病人脑中存在神经递质——乙酰胆碱(ACh)——大量缺失的现象，而这与乙酰胆碱酯酶(AChE)有极大的关系，它能促进神经系统中ACh的降解，因此可通过AChE受体抑制剂来提高患者病区的ACh水平来治疗AD。我们设计并合成了一类哌嗪类化合物，以期望获得一种毒副作用低、疗效高的潜在的治疗AD的药物。它们的AChE抑制活性正在评估。
第四章研究了碘代二茂铁与苯基硼酸在钯催化下的插羰反应来合成芳基二茂铁基酮。芳基二茂铁基酮典型的合成方法是通过二茂铁的酰化反应，但这一方法在制得单酰基二茂铁的同时，通常会有二取代的产物生成。与Friedel-Crafts酰基化方法相比，我们采用的碘代二茂铁与苯基硼酸的羰基化偶联反应，很好的得到了单一产物。
This thesis consists of four chapters.
The first chapter is to review the synthesis of 1,2,3-triazoles. 1,2,3-Triazoles are attractive constructs, which have be attented widely. Up to now, they have not been isolated from natural products. We summarize methods for synthesis of 1,2,3-triazoles. 1,3-Dipolar cycloaddition of azides to alkynes is the most important one of them, which was first proposed and studied by Rolf Huisgen. Then Sharpless and Fokin et al developed copper(I)-catalyzed cycloaddition reaction for synthesis of 1,2,3-triazoles.
In the second chapter, a series of 1,4,5-trisubstituted 1,2,3-triazoles has been prepared simply and conveniently via 1,3-dipolar cycloaddition/coupling reaction of terminal alkynes, phenylboronic acids and sodium azide in 1,4-dioxane-water using CuI/CuSO_4 as catalyst. In this part, a novel method for synthesizing 1,4,5-trisubstituted 1,2,3-triazoles directly from a variety of phenylboronic acids, sodium azide, and some terminal alkynes has been developed. The procedure does not require isolating of the azide intermediates and it shows a series of advantages, for example, it is safe, efficient, convenient and environmentally benign.
In the third chapter, some potential agents for Alzheimer's disease (AD) have been designed and synthesized. The neurodegenerative AD has been recognized as one of the most severe conditions affecting the aged and is life-threatening for this group of people. At the cellular, AD is associated mainly with reduced levels of synaptic acetylcholine (ACh) and other related neurotransmitters. Acetylcholinesterase (AChE) is the enzyme involved in the hydrolysis of the neurotransmitter ACh at cholinergic synapses in the central and peripheral nervous systems. So, a palliative treatment of AD is possible by the use of agents that restore the level of ACh. Inhibitors of AChE activity promote an increase in the concentration and the duration of action of the cholinergic transmission through activation of the synaptic nicotinic and muscarinic receptors. In this part, a series of piperazine compounds has been designed and synthesized, and their AChE inhibitory activity is being evaluated.
In the fourth chapter, a series of aryl ferrocenyl ketones has been prepared from iodoferrocene, phenylboronic acids and CO via palladium-catalyzed carbonylation coupling in a short time. The typical procedure for preparing aryl ferrocenyl ketones was via Friedel-Crafts acylation of ferrocene, yet it often afforded a mixture of mono- and di-acylated derivatives together with unreacted starting material. The method avoided formation of di-acylated derivatives compared with currently available Friedel-Crafts acylation methodologies.
第一章对1，2，3-三唑的合成方法进行了介绍。1，2，3-三唑因为其独特的化学特性和结构，已经引起了广泛重视。目前为止，我们还没有从天然产物中分离到含1，2，3-三唑环结构的化合物。本文对不同的合成方式进行了总结，其中以Huisgen首先提出的叠氮化物与炔的1，3-偶极环加成反应最为重要。近年，Sharpless，Fokin等发展了Cu(I)催化的环加成合成1，2，3-三唑的反应。
第二章研究了在1，4-二氧六环和水的混合溶剂中CuI／CuSO_4催化的末端炔、苯基硼酸和叠氮钠的1，3-偶极环加成偶联反应，合成了一系列1，4，5-三取代的1，2，3-三唑。本章介绍了一种新颖的从苯基硼酸，叠氮钠及部分的末端炔合成1，4，5-三取代的1，2，3-三唑的方法，从而很好的避免了制备和分离有机叠氮的操作，因此这一方法显示了许多的优点，如安全、有效、操作方便、环境友好等。
第三章设计并合成了一类潜在的治疗老年痴呆症(AD)的化合物。AD已经成为威胁老年人生活质量和生命的主要疾病之一。在细胞水平上，AD病人脑中存在神经递质——乙酰胆碱(ACh)——大量缺失的现象，而这与乙酰胆碱酯酶(AChE)有极大的关系，它能促进神经系统中ACh的降解，因此可通过AChE受体抑制剂来提高患者病区的ACh水平来治疗AD。我们设计并合成了一类哌嗪类化合物，以期望获得一种毒副作用低、疗效高的潜在的治疗AD的药物。它们的AChE抑制活性正在评估。
第四章研究了碘代二茂铁与苯基硼酸在钯催化下的插羰反应来合成芳基二茂铁基酮。芳基二茂铁基酮典型的合成方法是通过二茂铁的酰化反应，但这一方法在制得单酰基二茂铁的同时，通常会有二取代的产物生成。与Friedel-Crafts酰基化方法相比，我们采用的碘代二茂铁与苯基硼酸的羰基化偶联反应，很好的得到了单一产物。
This thesis consists of four chapters.
The first chapter is to review the synthesis of 1,2,3-triazoles. 1,2,3-Triazoles are attractive constructs, which have be attented widely. Up to now, they have not been isolated from natural products. We summarize methods for synthesis of 1,2,3-triazoles. 1,3-Dipolar cycloaddition of azides to alkynes is the most important one of them, which was first proposed and studied by Rolf Huisgen. Then Sharpless and Fokin et al developed copper(I)-catalyzed cycloaddition reaction for synthesis of 1,2,3-triazoles.
In the second chapter, a series of 1,4,5-trisubstituted 1,2,3-triazoles has been prepared simply and conveniently via 1,3-dipolar cycloaddition/coupling reaction of terminal alkynes, phenylboronic acids and sodium azide in 1,4-dioxane-water using CuI/CuSO_4 as catalyst. In this part, a novel method for synthesizing 1,4,5-trisubstituted 1,2,3-triazoles directly from a variety of phenylboronic acids, sodium azide, and some terminal alkynes has been developed. The procedure does not require isolating of the azide intermediates and it shows a series of advantages, for example, it is safe, efficient, convenient and environmentally benign.
In the third chapter, some potential agents for Alzheimer's disease (AD) have been designed and synthesized. The neurodegenerative AD has been recognized as one of the most severe conditions affecting the aged and is life-threatening for this group of people. At the cellular, AD is associated mainly with reduced levels of synaptic acetylcholine (ACh) and other related neurotransmitters. Acetylcholinesterase (AChE) is the enzyme involved in the hydrolysis of the neurotransmitter ACh at cholinergic synapses in the central and peripheral nervous systems. So, a palliative treatment of AD is possible by the use of agents that restore the level of ACh. Inhibitors of AChE activity promote an increase in the concentration and the duration of action of the cholinergic transmission through activation of the synaptic nicotinic and muscarinic receptors. In this part, a series of piperazine compounds has been designed and synthesized, and their AChE inhibitory activity is being evaluated.
In the fourth chapter, a series of aryl ferrocenyl ketones has been prepared from iodoferrocene, phenylboronic acids and CO via palladium-catalyzed carbonylation coupling in a short time. The typical procedure for preparing aryl ferrocenyl ketones was via Friedel-Crafts acylation of ferrocene, yet it often afforded a mixture of mono- and di-acylated derivatives together with unreacted starting material. The method avoided formation of di-acylated derivatives compared with currently available Friedel-Crafts acylation methodologies.
引文
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