Copper-catalyzed synthesis of aminoquinolines from β-(2-aminophenyl)-α,β-ynones using DMF as dual synthon
Balaji Ganesan, Karthick Govindan, Gopal Chandru Senadi, Mohanraj Kandasamy, Wei‐Yu Lin
Abstract
A new and efficient method has been developed for the synthesis of 4-aminoquinoline through aerobic Cu(i)-catalyzed cyclization of β-(2-aminophenyl)-α,β-ynones. Under the optimized conditions, DMF could serve as a methine source to introduce C2 carbon and a nitrogen source to incorporate amino functionality in the 4th position. Mechanistic studies using 13C- and DMF-d7 revealed that the methine group was derived from a methyl substituent.
Topics & Concepts
SynthonCatalysisChemistryQuinolineCombinatorial chemistryDual (grammatical number)CopperCarbon fibersAminoquinolinesNitrogenOrganic chemistryMaterials scienceLiteratureComposite materialComposite numberArtCatalytic C–H Functionalization MethodsCatalytic Alkyne ReactionsCyclopropane Reaction Mechanisms