新型茶香酮-氧化吲哚类拼接物的合成

Synthesis of Ketoisophorone-oxindole Hybrids

本文基于新的方法学研究,以氧化吲哚(1)与茶香酮(2)为原料,在DABCO和哌啶组合催化体系下,在溶剂乙醇65℃中发生Michael加成脱氢反应,合成了10个未见文献报道的茶香酮-氧化吲哚类拼接物3a~3j,产率为52%~71%,其结构经^(1)H NMR,^(13)C NMR和HR-MS(ESI-TOF)表征,进一步通过单晶确定化合物3e的相对构型。该类化合物包含一个具有潜在生物活性的茶香酮骨架和氧化吲哚骨架,可以为生物活性筛选提供物质基础。

In this paper,based on the new methodology,Ten new ketoisophorone-oxindole hybrids 3a~3j were synthesized via a Michael addition/dehydrogenation reaction of oxindole 1 and ketoisophorone 2 in solvent ethanol at 65℃under the combined catalytic system of DABCO and piperidine.The yields of 3a~3j were 52%~71%.The structures of products were characterized by^(1)H NMR,^(13)C NMR and HR-MS(ESI-TOF).The configuration of compound 3e was further determined by the single crystal.These compounds include a potential bioactive oxindole skeleton and ketoisophorone skeleton,which can provide a material basis for bioactivity screening.