Base‐Promoted Synthesis of Polysubstituted 4‐Aminoquinolines from Ynones and 2‐Aminobenzonitriles under Transition‐Metal‐Free Conditions
Ankit Kumar, Pawan K. Mishra, Kapil Mohan Saini, Akhilesh K. Verma
Abstract
Abstract A transition‐metal‐free and base‐promoted one‐pot reaction of ynones with 2‐aminobenzonitriles is described. The reaction was initiated through sequential aza‐Michael addition/intramolecular annulation to afford various multisubstituted 4‐aminoquinolines and 4‐amino‐1,8‐naphthyridines in good to excellent yields. Operational simplicity, high atom‐economy with broad substrate scope makes this protocol more attractive. Also, the gram‐scale synthesis and further transformation of the product were studied. Additionally, 2‐haloarylyones as substrate provide N‐arylquinolones as the sole product via the S N Ar mechanism. magnified image
Topics & Concepts
ChemistryIntramolecular forceAnnulationCombinatorial chemistrySubstrate (aquarium)Atom economyTransition metalBase (topology)Scope (computer science)Organic chemistryStereochemistryCatalysisComputer scienceGeologyProgramming languageOceanographyMathematicsMathematical analysisCatalytic C–H Functionalization MethodsCatalytic Alkyne ReactionsSulfur-Based Synthesis Techniques