新型水溶性希夫碱化合物的合成

Synthesis of Novel Water-Soluble Schiff's Base Compounds

从绿色化学的角度出发,实现水相中过渡金属催化的偶联反应已经成为人们研究的热点。希夫碱作为配位催化反应的重要配体,对其水溶性结构的设计合成研究具有重要的意义。本文通过五步反应:首先利用邻苯二甲酰亚胺钾盐与长链二溴烷烃发生单取代反应,得到N-溴烷基取代邻苯二甲酰亚胺产品,然后与三乙胺的乙醇溶液作用生成N-烷基季铵盐取代邻苯二甲酰亚胺化合物,进一步水解得到季铵盐取代的长链氨基溴化氢产物,最后与水杨醛缩合脱水得到两种新型水溶性希夫碱化合物,总收率分别为40%和33%。通过核磁氢谱对产品进行表征,确定其结构。该合成方法具有反应条件温和,产率较高,操作简单等优点;该配体在过渡金属催化的C-C、C-N偶联反应具有潜在的应用价值。

From the perspective of green chemistry,the transition metal-catalyzed coupling reactions in water has become a hot research. Schiff base with water-soluble structure as an important ligand in catalytic reactions is of great significance. In this paper,two novel water-soluble Schiff base compounds were obtained by five steps reactions. Potassium salt of phthalimide reacted with a long chain dibromoalkanes to give N-bromo-substituted alkyl phthalimide products,and then N-alkyl substituted quaternary ammonium salts of phthalimide were generated in the presence of ethanol solution of triethylamine. Followed by hydrolysis gave ammonium salt with a long-chain quaternary ammonium group,and condensation with salicylaldehyde to afford two novel Schiff＇s base compounds in the total yields of 40% and 33% respectively. The products were characterized by 1H NMR spectroscopy. This synthetic method has the advantages of mild reaction conditions, high yields, and easy operation.