N-杂环化合物的芳基化反应研究

发布时间：2018-08-08 11:54

【摘要】：N-杂环化合物是一类重要的有机物,它在天然产物、药物、农药以及相关材料的合成当中的应用非常广泛,其中芳基取代的N-杂环化合物(以芳基吡啶和芳基喹啉为主)因具有多样的生物活性及应用价值而受到关注。对于芳基N-杂环化合物的合成,最普遍的方法是在过渡金属的催化下,卤代N-杂环化合物与不同的芳基化试剂进行反应得到芳基取代的N-杂环化合物,其中芳基化试剂主要包括芳基非金属及金属化合物(以苯硼酸最为常用)、芳基亚磺酸盐以及苯。这些合成方法虽然极大地促进了N-杂环化合物芳基化的发展,但都存在一些不足之处。为了解决这些问题,我们发展了一种新的合成芳基N-杂环化合物的方法,该方法以PdCl2/Cs2CO3为催化体系,以高价碘化合物为芳基化试剂对溴代N-杂环化合物进行芳基化,合成了芳基吡啶、芳基喹啉等芳基化产物。该方法不需要配体的参与,反应条件简单温和,操作简便,底物适应性好且产物产率较高,最主要的是高价碘化合物容易制备价格便宜,而且毒性低对环境友好,因而该方法在N-杂环化合物芳基化反应中更具有优越性。
[Abstract]:N-heterocyclic compounds are important organic compounds, which are widely used in the synthesis of natural products, drugs, pesticides and related materials. Aryl substituted N-heterocyclic compounds (mainly aryl pyridine and aryl quinoline) have attracted much attention due to their diverse biological activities and application value. For the synthesis of aryl N-heterocyclic compounds, the most common method is to react halogenated N-heterocyclic compounds with different arylation reagents under the catalysis of transition metals to obtain N-heterocyclic compounds with aryl substitutions. Arylation reagents mainly include aryl nonmetallic and metal compounds (most commonly used in phenylboric acid), aryl sulfonates and benzene. Although these synthetic methods have greatly promoted the development of N-heterocyclic compounds arylation, they all have some shortcomings. In order to solve these problems, we have developed a new method for the synthesis of aryl N-heterocyclic compounds. The method uses PdCl2/Cs2CO3 as catalytic system and high-valence iodine compounds as arylation reagents for the arylation of brominated N-heterocyclic compounds. Arylation products such as aryl pyridine and aryl quinoline were synthesized. The reaction conditions are simple and mild, the operation is simple, the substrate is adaptable and the yield of the product is high. The most important thing is that the high valence iodine compound is easy to be prepared at low cost and low toxicity to the environment. Therefore, this method has more advantages in the arylation reaction of N-heterocyclic compounds.
【学位授予单位】：兰州大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O621.25

【相似文献】