银催化邻炔基苯甲醛腙合成多取代异喹啉偶极子

将含有不同取代基团的邻炔基苯甲醛腙化合物在乙酸银催化下,以二氯甲烷作溶剂,室温下自身发生环化反应合成N,N-异喹啉偶极子化合物。通过质谱(MS)、核磁共振波谱仪(NMR)等技术手段表征化合物的结构。考察了不同催化剂及其用量、原料配比、溶剂、温度对反应的影响。在最优条件下,反应收率为60%,在底物适应性上最高可达到85%。该方法具有操作简单,反应条件简单温和,产物收率高以及底物适用性好等优点。本文通过对实验条件、底物适用性等方面的探索,解决了以往合成异喹啉偶极子方法学中存在的多步进行、反应温度过高、底物适应性较低等不足与缺点,为制备含此类骨架的化合物提供了新的实验方法。

Synthesis of N,N-Isoquinoline Dipoles via Intramolecular Cyclization of o-Alkynylbenzaldehyde Hydrazones

N,N-Isoquinoline dipole derivatives were synthesized via intramolecular cyclization of o-alkynylbenzaldehyde hydrazones in the presence of silver acetate(AgOAc) in dichloromethane(DCM) at room temperature. The chemical structures of these obtained products were characterized by mass spectrometry and nuclear magnetic resonance spectroscopy(NMR). In addition, the effect of catalysts and their loadings, raw material ratios, solvents and temperatures on the yields was investigated. The target compound (3-(((methoxycarbonyl)oxy)methyl)isoquinolin-2-iu-m-2-yl)(tosyl)-amide is obtained in 60% yield and the substrate adaptability can be up to 85% under optimum conditions. This method has advantages of easy operation, mild reaction condition and functional group tolerance. Through the exploration of experimental conditions and substrate applicability, this paper solves the disadvantages and shortcomings of the method of synthesizing isoquinoline dipole compounds in the past, which provides a new experimental method for the preparation of compounds containing such skeletons.