靛红衍生物与水杨醛的串联反应

The Tandem Reaction of Isatin Derivatives with Salicyl Aldehyde

以靛红为原料,通过Wittig反应合成了两种不同取代基的靛红衍生物。再通过这两种靛红衍生物与水杨醛发生串联Michael-Aldol反应,高效的构建了螺[5,6]环的骨架结构。通过对照实验,总结了取代基团对靛红与水杨醛的Michael-Aldol反应的影响。通过筛选不同的碱和溶剂,最终确定在K2CO3、DMF、室温条件下以62%的产率得到目标分子。产物都经1H-NMR、13CNMR进行表征,目标分子还用X-射线单晶衍射表征。

The tandem reactions of salicylic aldehydes with α,β - unsaturated compounds have only been studied systematically in recent years. Bioactive oxindole derivatives with salicylic aldehydes have not been reported yet. Our team first use tandem reaction of these two compounds,successfully and effectivly build a spiro -[5,6]benzopyrrole skeleton. The product was verified by 1^ H - NMR 13^C - NMR and X - ray crystal structure analysis.