串联[3+2]环加成和丁炔二甲酸酯参与的扩环反应合成新型螺吲哚酮和螺二氢喹啉类化合物

Synthesis of Novel Spirooxindole and Spirodihydroqinoline by Domino[3+2]Cycloaddition and Acetylenedicarboxylate Promoted Ring-expansion Reaction

因具有原料易得、方法简便、反应步骤和分离步骤少等特点,多组分反应和串联反应在有机合成中获得广泛的应用。本文报道一种简洁高效的串联反应合成螺环化合物的新方法。通过硫代脯氨酸、靛红和双查尔酮先在甲醇中进行[3+2]环加成反应,然后在甲醇回流条件下与丁炔二酸二甲酯通过扩环反应,分别生成了结构新颖的含巯基的螺吲哚酮化合物和螺二氢喹啉衍生物,其结构经IR,HR-MS,^(1)H NMR和^(13)C NMR表征,并确定了单晶分子结构。该反应具有原料简单易得,操作简便,原子经济性高等优点。

Multicomponent reaction and domino reaction are widely used in organic synthesis because of their using readily available raw materials,convenient synthetic method,less reaction steps and separation processes.a simple and efficient method for synthesizing spiro compounds via domino reaction was reported in this paper.The one-pot[3+2]cycloaddition reaction of L-thioproline,isatins and chalcones and sequential ring-expansion reaction with dimethyl but-2-ynedioate in refluxing methanol resulted in sulfanyl-containing polycyclic spirooxindole and spirodihydroqinoline derivatives.The spiro compounds were characterized by IR,HR-MS,^(1)H NMR and ^(13)C NMR spectroscopy and were confirmed by single crystal structures.The formation mechanism of the two compounds included domino ring-opening and annulation process.This reaction has the advantages of using readily available substrates,simple operation and high atomic economy.