硫-Michael串联反应构建含氮杂环化合物的研究

发布时间：2018-03-24 06:25

本文选题：吡啶衍生物　切入点：吲哚里西啶类衍生物　出处：《吉林大学》2017年硕士论文

【摘要】：含氮杂环化合物在药物,材料,催化等方面有着诸多应用,其中具有吲哚里西啶结构单元化合物与具有季碳中心的吡啶化合物占有重要比重。合成此类化合物的过程中存在着条件比较苛刻,操作复杂,反应效率较低等缺点。因此研究高选择性,高产率的合成此类杂环化合物的方法具有重要意义。基于以上背景,本论文主要包括以下两个研究内容:1.设计并发展以烯丙基取代的1,2-二氢吡啶Ressert产物为底物,采用硫-Michael串联反应合成含有吲哚里西啶结构单元化合物。筛选了不同溶剂和不同类型的引发剂,确立了最优的反应条件。并且对底物进行扩展,考察此方法的普适性。该方法反应条件温和,立体选择性高,原子经济性高。2.设计并发展以烯丙基取代的1,2-二氢吡啶Ressert产物为底物,采用硫-Michael串联反应,亲核试剂对新构建酰胺键进攻,“一锅法”合成具有季碳中心官能团化的吡啶类衍生物。筛选了不同类型亲核试剂体系,确定反应条件,进而对底物进行扩展,最后做了一个简单而实用的转化实验。
[Abstract]:Nitrogen-containing heterocyclic compounds have many applications in medicine, materials, catalysis, etc. The structure unit compounds with indocyridine and pyridine compounds with quaternary carbon centers occupy an important proportion. The conditions for the synthesis of such compounds are harsh and the operation is complex. Therefore, it is important to study the method of synthesis of such heterocyclic compounds with high selectivity and high yield. This thesis mainly includes the following two research contents: 1. Design and development of Ressert products with allyl substituents as substrates. The structure unit compounds containing indocyridine were synthesized by the series reaction of sulfur and Michael. Different solvents and different initiators were screened, the optimum reaction conditions were established, and the substrate was extended. The method was characterized by mild reaction conditions, high stereoselectivity and high atomic economy. 2. The thio-Michael series reaction was designed and developed with allyl substituted 1-dihydropyridine Ressert product as substrate. The nucleophilic reagent attacked the newly constructed amide bond and synthesized pyridine derivatives with quaternary carbon center functionalization by "one pot" method. Different nucleophilic reagent systems were screened, reaction conditions were determined, and the substrate was expanded. Finally, a simple and practical conversion experiment is made.
【学位授予单位】：吉林大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O626

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