3-(5-芝麻酚)-3-羟基氧化吲哚拼接衍生物和芝麻酚并吡喃螺环氧化吲哚拼接衍生物的合成研究

The synthesis of Novel 3-(5-Sesamol)-3-Hydroxyoxindoles and Spiro-Fused Pyranyl benzo[d][1,3]dioxol Oxindoles

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）.