DDQ介导的新型3-吲哚烷酮及吡喃酮并[2,3-b]吲哚类化合物的合成

DDQ-Mediated Synthesis of Novel 3-Indolanone and Pyrano[2,3-b]Indoles

以1-(1 H-吲哚-3-基)戊烷-3-醇及其衍生物为底物,以三氟甲磺酸铜为催化剂,甲醇为溶剂,DDQ(2,3-二氯-5,6-二氰基对苯醌)为氧化剂,共合成9个新型的3-吲哚烷酮衍生物及5个结构新颖的吡喃酮并[2,3-b]吲哚衍生物,其结构经1 H NMR,13 C NMR和HR-MS(ESI)表征。对反应机理进行了推测并通过同位素实验进行了验证,反应为碳正离子参与并经分子间和分子内的亲核加成形成碳-氧键的过程。

With 1-(1 H-indole-3-yl)pentane-3-ol and its derivatives as substrates,copper triflate as catalyst,methanol as solvent,and DDQ(2,3-dichloro-5,6-dicyano-p-benzoquinone)as oxidant,a total of nine novel 3-indolinone derivatives and five novel pyranone[2,3-b]indole derivatives were synthesized.Their structures were characterized by 1 H NMR,13 C NMR and HR-MS(ESI).The reaction mechanism has been speculated and verified by isotope experiments.The reaction is a process in which carbocations participate and form carbon-oxygen bonds through intermolecular and intramolecular nucleophilic addition.