三氯化铝催化炔酰胺和邻亚甲基苯醌的环加成反应

发布时间：2018-08-23 11:41

【摘要】：炔酰胺由于其独特的分子结构,很好地兼顾了炔基的稳定性和反应活性间的关系,而且在化学反应中又体现了良好的区域选择性,因而在有机合成方法学、天然产物全合成、特别是含氮化合物的合成方面有很大的优势。炔酰胺的环加成反应是一种能够高效地合成单环或是多环化合物的方法,然而之前关于炔酰胺的环加成反应的研究多是生成碳环类化合物,而关于杂环化合物的合成报道相对较少。因此,进一步研究炔酰胺在杂环化合物合成中的应用对于该类化合物的合成研究非常重要。胺基取代色烯(苯并吡喃)结构作为很多天然产物和药物中常见的组成单元,其合成方法一直受到广泛关注。然而,由于传统的胺基色烯类化合物的合成方法相对单一,所以已报道的该类化合物相对较少。在本文中,我们使用AlCl3催化炔酰胺和邻亚甲基苯醌的环加成反应合成不同类型胺基取代的色烯类化合物。分别以炔基末端带有取代基的炔酰胺和邻亚甲基苯醌进行环加成反应以很好是收率和很高的非对映选择性得到4-胺基-2H-色烯类化合物;炔基末端不含取代基的炔酰胺和邻亚甲基苯醌反应以很好是收率得到2-胺基-4H-色烯类化合物。该方法为多种胺基取代色烯类化合物的合成提供了便捷高效的途径。
[Abstract]:Because of its unique molecular structure, acetylidene takes into account the relationship between the stability of acetylene group and the reaction activity, and shows good regioselectivity in chemical reaction. Therefore, in the organic synthesis methodology, natural products are fully synthesized. In particular, the synthesis of nitrogenous compounds has great advantages. The cycloaddition reaction of acetylene amides is a method that can efficiently synthesize monocyclic or polycyclic compounds. However, previous studies on cycloaddition reactions of acetylidene amides have been focused on the formation of carbon-ring compounds. However, there are few reports on the synthesis of heterocyclic compounds. Therefore, it is very important to study the application of acetylene amide in the synthesis of heterocyclic compounds. Amino substituted chromotene (benzopyran) structure as a common component of many natural products and drugs, its synthesis methods have been widely concerned. However, due to the traditional synthesis method of aminochromene compounds is relatively simple, so reported relatively few of these compounds. In this paper, AlCl3 was used to catalyze the cycloaddition reaction of acetylidene amide and o-methylene benzoquinone to synthesize different amine-substituted chromene compounds. 4-amino-2H-chroene compounds were synthesized by cycloaddition reaction of acetylidene amide with substituted group at the end of acetylene group and o-methylene benzoquinone in good yield and high enantioselectivity. 2-amino-4H-chroene compounds were obtained by the reaction of alkyne amide with o-methylene benzoquinone without substituents at the end of acetylene group in good yield. This method provides a convenient and efficient way for the synthesis of various amino substituted chromene compounds.
【学位授予单位】：郑州大学
【学位级别】：硕士
【学位授予年份】：2016
【分类号】：O621.256.7

【相似文献】