以取代靛红作为起始原料,通过和芝麻酚在10 mol%DABCO催化剂和二氯甲烷溶剂条件下的Aldol反应,高效合成3个未见文献报道的3-(5-芝麻酚)-3-羟基氧化吲哚(2a~2c),产率为85%-92%。以取代靛红作为起始原料,通过和芝麻酚以及丙二腈在10 mol%DABCO催化剂和二氯甲烷溶剂条件下的三组分Domino反应,高效合成5个未见文献报道的芝麻酚并吡喃螺环氧化吲哚(3a-3e),产率为87%-94%。底物取代基结构经1H NMR,13C NMR和MS(ESI)表征。
Sesamol and various substituted isatins were catalyzed by 10 mol% DABCO in CH2Cl2 at room temperature via Aldol reaction. Three unreported 3-(5-sesamol)-3-hydroxyoxindoles(2a - 2c) were obtained with yields of 85% - 92%. Sesamol,malononitrile and various substituted isatins were catalyzed by DABCO in CH2Cl2 at room temperature via Domino reaction. Five unreported spiro-fused pyranyl benzo[d][1,3]dioxol oxindoles(3a - 3e) were synthesized efficiently with yields of 87% - 94%. In this paper we also discussed the relationship between reaction rate and substituent groups in such reactions. The structures of substituent group of substrates were characterized by1 H NMR,13 C NMR and MS(ESI).