色酮吡唑啉酮骨架拼接二氢查尔酮类化合物的合成

Synthesis of of Pyrazolone-Chromone-Dihydrochalcone Hybrids

以色酮-吡唑啉酮合成子(1)为原料,在三级胺N,N-二甲基乙醇胺催化下,与查尔酮发生Michael加成反应,合成了10个新型的色酮吡唑啉酮骨架拼接二氢查尔酮类化合物3a~3j,产率79%~90%,dr值为6/1~10/1,其结构经^(1)H NMR,^(13)C NMR和HR-MS(ESI-TOF)表征。化合物3b的相对构型由单晶培养确定。该类化合物含有连续两个立体中心,包括一个季碳中心,可以为生物活性筛选提供物质基础。

In this paper,the Michael addition reaction of pyrazolone-chromones with chalcones was investigated for the first time,using DABCO as an organic catalyst,to provide a variety of potentially bioactive pyrazolone-dihydrochalcone adducts(3a~3j)in 79%~90%yield and dr 6/1~10/1.The structures were characterized by ^(1)H NMR,^(13)C NMR and HR-MS(ESI-TOF).The relative configuration of compound 3b was further determined by the single crystal.These compounds bear two contiguous stereogenic centers,including one quaternary carbon center.It can provide material basis for biological activity screening.