邻溴苯胺/丙烯醛Schiff碱分子内Heck反应——合成喹啉的新方法

A new method to synthesize quinoline via intramolecular Heck reaction of Schiff base made from o-bromoaniline and acraldehyde

探讨了一种以邻溴苯胺和丙烯醛为原料合成喹啉的新方法,对反应条件进行了优化,并利用质谱和红外光谱分析确认了合成产物的结构.结果表明,以邻溴苯胺和丙烯醛为原料,经2步反应可得到喹啉:首先,邻溴苯胺和丙烯醛反应生成Schiff碱;随后,Schiff碱在催化剂和N2保护下经分子内Heck反应形成目标产物(总产率为45.1%).该合成方法具有操作简单、易于控制、催化剂可重复使用等优点.

A new method was explored to synthesize quinoline with 2-bromoaniline and acraldehyde as the starting materials.The reaction conditions were optimized,and the structure of as-synthesized quinoline was confirmed by means of mass spectrometry and infrared spectrometry.It has been found that quinoline can be prepared via two-step reactions of raw materials of 2-bromoaniline and acraldehyde.Namely,2-bromoaniline and acraldehyde react to form Schiff base at the first step.Resultant Schiff base is then allowed to participate in intramoleculalr Heck reaction with the assistance of catalyst in nitrogen atmosphere yielding target product in a total yield of 45.1%.The establish method is dominated by simple procedure,easy operation,and recyclability of catalyst.