Iodine Catalyzed C2‐H Formamidation of Quinoline N‐Oxides using Isocyanides: A Metal‐Free Approach

Abstract

A molecular iodine catalyzed regioselective insertion of isocyanide into C2-H of quinoline N-oxides has been developed. The reaction proceeds through the nucleophilic addition of isocyanide on quinoline Noxides followed by rearrangement in presence of iodine. This metal-free reaction affords rapid access to quinoline 2-formamides with exceptional functional group tolerance, broad substrate scope and 100% atomeconomy. A library of 33 N-(2-quinolinyl)formamides are synthesized, which may find applications in pharmaceuticals and synthetic chemistry.

Advances in gold catalyzed synthesis of quinoid heteroaryls

“…1,[74][75][76][77][78][79][80][81] Recent methods utilizing ionic liquids or ester-radical methyl carbamate offer improved substrate scope and milder conditions compared to traditional approaches. [82][83][84][85][86][87] These advancements facilitate the construction of highly functionalized (quinolinyl)amides from quinoline N-oxides and nitriles. 88…”

“…1,74–81 Recent methods utilizing ionic liquids or ester-radical methyl carbamate offer improved substrate scope and milder conditions compared to traditional approaches. 82–87 These advancements facilitate the construction of highly functionalized (quinolinyl)amides from quinoline N -oxides and nitriles. 88 Wu, Jiawen et al , studied a gold-catalyzed redox-neutral reaction between 8-methyl quinoline N -oxide ( 2d ) and 3-phenyl propane nitrile ( 2e ) yielded N -acylated 2-aminoquinoline ( 2f ) in high yields (Scheme 6).…”

Recent Advances in Cyclization Reactions of 1,6‐Enynes

“…[5] Compared with the conventional methods, metal-free catalyzed reactions avoided the use of precious transition metal catalysts, has been dedicated to the modularized construction of valuable, architecturally complex, and functionalized frameworks, providing a greater diversity of organic compounds for drug discovery. [6] In addition, electrocatalytic cyclization reactions have provided approaches for accessing functionalized frameworks from readily available substrates with the advantages of high efficiency, atomic economy and operational simplicity. [7] Cascade cyclization strategies emerging as efficient approaches for accessing synthetically versatile skel-etons, have gained special interest from organic synthetic chemists owing to the straight and simple synthesis logic.…”

N-Oxide-Induced Ugi Reaction: A Rapid Access to Quinoline-C2-amino Amides via Deoxygenative C(sp2)–H Functionalization

“…In the continuation of our work on C2–H functionalization of aromatic amine N -oxides using isocyanides, herein we report a N -oxide-induced Ugi reaction to access a library of 2-phenyl-2-(phenyl­(quinolin-2-yl)­amino)­acetamide derivatives in one-pot reactions via C­(sp 2 )–H functionalization.…”