Three-Component Synthesis of 2-Substituted Quinolines and Benzo[<i>f</i>]quinolines Using Tertiary Amines as the Vinyl Source
Yanfeng Ma, Chunlan Zhou, Fuhong Xiao, Guojiang Mao, Guo‐Jun Deng
Abstract
A metal-free method for the construction of 2-substituted quinolines and benzo[ f ]quinolines from aromatic amines, aldehydes, and tertiary amines has been demonstrated. Cheap and readily available tertiary amines acted as the vinyl source. A new pyridine ring was selectively formed via [4 + 2] condensation that was promoted by ammonium salt under neutral conditions and an oxygen atmosphere. This strategy provided a new route for the preparation of various quinoline derivatives with different substituents at the pyridine ring, which provides the possibility of further modification.
Topics & Concepts
QuinolineChemistryPyridineRing (chemistry)CondensationAmmoniumSalt (chemistry)Tertiary amineOrganic chemistryAmmonium acetateMedicinal chemistryCombinatorial chemistryPhysicsHigh-performance liquid chromatographyThermodynamicsCatalytic C–H Functionalization MethodsCyclopropane Reaction MechanismsSynthesis and Reactivity of Heterocycles