Microwave-Assisted Domino Povarov-Type [4+2] Cycloaddition: A Rapid Access to 7-Phenyl-6H-chromeno[4,3-b]quinolines
Dakoju Ravi Kishore, Kurella Mounika, Gedu Satyanarayana, Komal Goel, Jakkula Naveen
Abstract
Abstract A convenient, facile, and eco-friendly approach to synthesizing 7-phenyl-6H-chromeno[4,3-b]quinolines under microwave irradiation is presented. The current strategy enabled the synthesis of chromenoquinoline frameworks at 80 °C under shorter reaction times via intermolecular Schiff base formation followed by an intramolecular inverse demand hetero-Diels–Alder [4+2]-cycloaddition reaction by using a catalytic amount of copper triflate as the sole catalyst. Consequently, one C–N and two C–C bonds are constructed in a single pot, and a wide spread of 7-phenyl-6H-chromeno[4,3-b]quinolines have been synthesized with good functional group tolerance.
Topics & Concepts
ChemistryCycloadditionIntramolecular forceIntermolecular forceDominoCatalysisTrifluoromethanesulfonateMicrowave irradiationCombinatorial chemistryMedicinal chemistrySchiff baseOrganic chemistryStereochemistryMoleculeMulticomponent Synthesis of HeterocyclesSynthesis of Organic CompoundsSynthesis and Biological Evaluation