新型吡唑及吲哚类稠杂环化合物的合成研究

发布时间：2018-04-05 17:07

本文选题：稠杂环化合物　切入点：吡唑　出处：《渤海大学》2017年硕士论文

【摘要】：吡唑和吲哚是非常重要的杂环化合物,在自然界分布广泛,拥有多种生物活性,已成为某些医药、农药生产的重要原料,具有广阔的研究和开发前景。因此,对新型吡唑及吲哚类杂环化合物的合成方法研究具有非常重要的意义。本论文主要分为四部分:第一部分,通过查阅大量的有关文献,以吡唑及吲哚为主要内容,介绍杂环化合物的合成方法、相关应用及选题依据和研究意义。第二部分,以2-苯基-3-甲基-4-乙酰基吡唑为起始物质,通过溴代反应得到中间体---2-苯基-3-溴甲基-4-乙酰基吡唑,并以其为新型吡唑类化合物的合成子探讨通过与含氰基的双功能基亲核试剂(水杨氰、巯基水杨氰、3-氰基吡啶硫酮)的缩合、异构化(Thorpe-Ziegler反应),实现吡唑类稠杂环化合物的合成新途径。第三部分,通过吲哚-3-甲醛与2-氨基吡啶、三甲基氰硅烷的环化反应(Groebke-Blackburn-Bienaymé反应),制备活性氨基化合物3-氨基-2-(吲哚-3-基)吡啶并咪唑,并进一步通过与醛的环化反应(Pictet-Spengler反应),实现吡啶并咪唑类咔啉稠杂环化合物的合成。第四部分,通过吲哚-3-甲醛与2-氨基吡嗪、三甲基氰硅烷的环化反应(Groebke-Blackburn-Bienaymé反应),制备活性氨基化合物3-氨基-2-(吲哚-3-基)吡嗪并咪唑,并进一步通过与醛的环化反应(Pictet-Spengler反应),实现吡嗪并咪唑类咔啉稠杂环化合物的合成策略。所有合成化合物的结构均通过红外谱图、核磁共振谱图予以表征。
[Abstract]:Pyrazole and indole are very important heterocyclic compounds. They are widely distributed in nature and have a variety of biological activities. They have become important raw materials for the production of certain medicines and pesticides and have a broad prospect of research and development.Therefore, it is of great significance to study the synthesis of new pyrazole and indole heterocyclic compounds.This paper is divided into four parts: the first part, by consulting a large number of related literature, taking pyrazole and indole as the main content, introduced the synthesis method of heterocyclic compounds, related applications, topics and research significance.In the second part, using 2-phenyl-3-methyl-4-acetylpyrazole as the starting material, the intermediate 2-phenyl-3-bromomethyl -4-acetylpyrazole was obtained by bromination reaction.The synthesis of new pyrazole compounds was studied by condensation with cyano containing bifunctional nucleophilic reagents (salicylidene, mercapto salicylidene 3-cyanopyridine thione).Thorpe-Ziegler reaction was used to realize the synthesis of pyrazole heterocyclic compounds.In the third part, the active amino compound 3-amino-2-( indole-3-yl) pyridine imidazole was synthesized by cyclization of indole-3-formaldehyde with 2-aminopyridine and trimethylcyanosilane, Groebke-Blackburn-Bienaym 茅.The synthesis of pyridine imidazole and carboline fused heterocyclic compounds was further achieved by the cyclization reaction of Pictet-Spengler with aldehydes.In the fourth part, the active amino-compound 3-amino-2-( indole-3-yl) pyrazinopyrazole was synthesized by the cyclization of indole-3-formaldehyde with 2-aminopyrazine and trimethylcyanosilane, Groebke-Blackburn-Bienaym 茅.Furthermore, the synthesis strategy of pyrazine-imidazoline-like carboline dense heterocyclic compounds was realized through the cyclization reaction of Pictet-Spengler with aldehydes.The structures of all the synthesized compounds were characterized by IR and NMR spectra.
【学位授予单位】：渤海大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O626

【参考文献】