2-苯甲酰基吲哚的合成研究

Investigation on the Synthesis of 2-Bezoylindole

2-苯甲酰基吲哚衍生物具有潜在的生物活性,但这文献中的合成方法还普遍存在一些缺点,如使用到昂贵的过渡金属、需无水无氧操作、原料不易得、不易放大操作等。从廉价易得的靛红和α-溴代苯乙酮出发经过N-取代再通过水解来制备通过对靛红的羰基进行保护、然后与α-溴代苯乙酮发生N-取代、再经过脱保护、碱性条件下水解环合4步反应可以高效地合成2-苯甲酰基吲哚。所得产物的结构通过NMR和MS进行了表征。

2-benzoylindole derivatives have potential biological activity, but there are some disadvantages in the reported synthetic methods,such as the use of expensive transition metals,anhydrous anaerobic operation,costly raw materials,and inconvenient to scale up.Herein,an efficient synthesis of 2-benzoylindole from isatine andα-bromoacetophenone was developed through successive protection of the carbonyl group of isatine,N-substitution reaction withα-bromoacetophenone,deprotection,and hydrolyitic cyclization.The structures of the generated products were fully characterized through their NMR and MS spectra.