2′,3′,4′,9′-四氢螺[吲哚啉-3,1′-吡啶并(3,4-b)吲哚]-2-酮的合成研究

Synthesis of 2',3',4',9'-tetrahydrospiro[indoline-3,1'-pyrido[3,4-b]indol]-2-one

在三氟乙酸催化下,色胺(化合物2)与靛红(化合物3)发生Pictet-Spengler反应,得到目标化合物2′,3′,4′,9′-四氢螺[吲哚啉-3,1′-吡啶并(3,4-b)吲哚]-2-酮(化合物1)。产物结构经1H-NMR、13C-NMR和MS表征。考察了影响该Pictet-Spengler反应的主要因素,确定的最佳反应条件为:n(三氟乙酸)∶n(化合物2)=0.8∶1,n(化合物3)∶n(化合物2)=1.2∶1,反应在甲苯中进行3h,化合物1的收率可以达到95.8%(以化合物2计)。

The target compound of 2',3',4',9'-tetrahydrospiro[indoline-3,1'-pyrido[3,4-b]indol]-2-one was synthesized from 2-(1H-indol-3-yl)ethan-1-amine(2)and indoline-2,3-dione(3)via Pictet-Spengler reaction under the catalysis of trifluoroacetic acid.The structures of product were characterized by'H-NMR,13C-NMR and MS.The main factors affecting the Pictet Spengler reaction conditions were investigated.The optimum reaction conditions were determined as follows:the dosage of trifluoroacetic acid was n(trifluoroacetic acid):n(2)=0.8:l,the material ratio was n(3):n(2)=1.2:1,the reaction was carried out in toluene for 3 hours,and the yield of product 1 reached 95.8%.