Aliphatic Alcohol Hydroxyl‐Directed One‐Pot Stepwise Synthesis: A Concise Synthesis of 1<i>H</i>‐pyrrolo[3,4‐<i>b</i>]quinoline‐1,3(2<i>H</i>)‐diones
Shuntao Huang, Qi Yang, Juan Wan, Zhuoyu Wang, Zhou Zhang, Teng Liu, Chao Huang
Abstract
Abstract A concise and flexible protocol to assemble structurally diverse 1 H ‐pyrrolo[3,4‐ b ]quinoline‐1,3(2 H )‐diones (29 examples, 70–87% yields) has been developed via one‐pot stepwise synthesis. The potentially valuable quinine‐fused heterocycles were synthetized by utilizing aliphatic alcohol hydroxyl as directing group which promoted a sequential transformation to form functionalized aminomaleimides, and then underwent an I 2 ‐oxidized tandem annulations. This route involved the formation of multiple new chemical bonds (C=N, 2C−N, C−C) in a one‐pot fashion under mild conditions.
Topics & Concepts
ChemistryQuinolineAlcoholTandemCombinatorial chemistryYield (engineering)Chemical synthesisStereochemistryOrganic chemistryMedicinal chemistryIn vitroComposite materialMetallurgyBiochemistryMaterials scienceCatalytic C–H Functionalization MethodsSynthesis of Indole DerivativesBioactive Compounds and Antitumor Agents