Iodine-imine Synergistic Promoted Povarov-Type Multicomponent Reaction for the Synthesis of 2,2′-Biquinolines and Their Application to a Copper/Ligand Catalytic System

Abstract

An efficient iodine-imine synergistic promoted Povarov-type multicomponent reaction was reported for the synthesis of a practical 2,2′-biquinoline scaffold. The tandem annulation has reconciled iodination, Kornblum oxidation, and Povarov aromatization, where the methyl group of the methyl azaarenes represents uniquely reactive input in the Povarov reaction. This method has broad substrate scope and mild conditions. Furthermore, these 2,2′-biquinoline derivatives had been directly used as bidentate ligands in metal-catalyzed reactions.

Recent advances in iodine–DMSO mediated C(sp3)–H functionalization of methyl-azaarenes via Kornblum oxidation

“…(Scheme 16). 37 For the sake of substrate scope investigation, several 2-methyl quinoline derivatives with electron-donating and withdrawing substituents were tested. All the substrates performed well in the reaction medium.…”

A Review on Molecular Iodine Catalyzed/Mediated Multicomponent Reactions

“…Hun et al [52] . reported a three‐component reaction of methylazarenes, amines and aldehydes in DMSO giving 2,2’‐biquinolines 42 (Scheme 22).…”

Recent Advances in Green Synthesis of Functionalized Quinolines of Medicinal Impact (2018‐Present)

“…This strategy involved a sequence of Iodination, Kornblum oxidation and Povarov aromatization with active mode of methyl azaarenes 165 (Scheme 45). [85] Aldehydes 166 and aromatic amines 167 were reacted in presence of iodine and mild base potassium carbonate in DMSO.…”