3-(3-香豆素基)丙烯醛的制备及其多组分反应构建双杂环化合物

Preparation of 3-(3-coumarinyl)Acrylaldehyde and Construction of Biheterocyclic Compounds by Multicomponent Reaction

用3-乙酰基香豆素与Vilsmeier试剂反应得到具有共轭结构且含有活泼醛基的3-(3-香豆素基)丙烯醛,考察了原料配比和反应温度对产率的影响,结果表明当3-乙酰基香豆素用量为4 mmol,三氯氧磷(POCl_(3))用量为1.6 mL,DMF用量8 mL,在60℃时产率最高。将合成的香豆素丙烯醛用于多组分反应中,构建了既含有香豆素环又含有吡啶/吡喃结构的7个双杂环化合物。对目标化合物的结构进行了红外、核磁、高分辨质谱表征,并对化合物Ⅱa进行了X-射线单晶衍射分析。

3-(3-coumarinyl)acrylaldehyde was synthesized by the reaction of 3-acetylcoumarin with Vilsmeier reagent.The effects of raw material ratio and reaction temperature were investigated.The results showed that the highest yield was obtained at 60℃when the dosage of 3-acetylcoumarin was 4 mmol,phosphorus oxychloride(POCl_(3))was 1.6 mL and DMF was 8 mL.The synthesized coumarin acrylaldehyde was used in the multicomponent reaction to construct seven biheterocyclic compounds containing both coumarin ring and pyridine/pyran structure.The structure of the target compounds were characterized by IR,NMR and HRMS,and compoundⅡa was analyzed by X-ray single crystal diffraction.