Self [3 + 4] Cycloadditions of Isatin N,N′-Cyclic Azomethine Imine 1,3-Dipole with N-(o-Chloromethyl)aryl Amides

• DOI: 10.1021/acs.joc.8b01055
• Publication Date: 2018-05-30T15:03:44Z
• Authors: Qiaomei Jin; Jian Zhang; Cuihua Jiang; Dongjian Zhang; Meng Gao; Shihe Hu
• Keywords: Isatin; Thiosemicarbazones; Cycloaddition Reaction; Antineoplastic Agents; Amides; 01 natural sciences; 3. Good health; 0104 chemical sciences; Inhibitory Concentration 50; Cell Line, Tumor; Humans; Imines; Azo Compounds

A [3 + 4] annulation of isatin N, N'-cyclic azomethine imine 1,3-dipole 1 with in situ-generated aza-oQMs has been established for the synthesis of spirooxindole seven-membered scaffolds. These highly functionalized scaffolds were assembled in moderate to good yields (up to 96% yield). The novel spirooxindole scaffolds displayed moderate antitumor activities, which represented promising lead compounds for antitumor drug discovery.