Intermolecular Amidation of Quinoline N-Oxides with Arylsulfonamides under Metal-Free Conditions

Abstract

An efficient method for the synthesis of N-(quinolin-2-yl)sulfonamides is described. The intermolecular amidation of quinoline N-oxides with sulfonamides proceeded smoothly in the presence of PhI(OAc) and PPh to afford N-(quinolin-2-yl)sulfonamides in satisfactory to excellent yields.

Recent Advances in the Synthesis of C2‐Functionalized Pyridines and Quinolines Using N‐Oxide Chemistry

“…Bao's group developed a new method to synthesize quinoline sulfonamides 111 from quinoline N-oxides, sulfonamides, PhI(OAc) 2 , and PPh 3 (Scheme 32). [54] The method is applicable to a variety of quinoline N-oxides and sulfonamides. Sulfonamides react with PhI(OAc) 2 to produce sulfonyl imino iodo arene 112 and acetic Ni-catalyzed sulfonamidation using N-fluorobenzenesulfonimide (NFSI, 115) as the amidating reagent was an efficient method described by Wu's group in 2019 (Scheme 33).…”

Recent Progress in Non‐Catalytic C–H Functionalization of Heterocyclic N‐Oxides

“…Amidation of quinoline N ‐oxides with sulfonamides has been found to proceed in the presence of PhI(OAc) 2 and PPh 3 through 1,3‐dipolar [3+3]‐cycloaddition as shown on Scheme 26. [ 50 ]…”

“…doi.org/10.1002/ejoc.202001115 Amidation of quinoline N-oxides with sulfonamides has been found to proceed in the presence of PhI(OAc) 2 and PPh 3 through 1,3-dipolar [3+3]-cycloaddition as shown on Scheme 26. [50] Scheme 26. Deoxygenative amidation of quinoline N-oxides with arylsulfonamides and proposed mechanism.…”

Hypervalent Iodine(III)‐Mediated Regioselective Cyanation of Quinoline N‐Oxides with Trimethylsilyl Cyanide

“…Iodine reagent as an eco-friendly and inexpensive reagent could induce functional groups to the 2-position of quinoline Noxides derivatives. [15] In 2017, Yu and colleagues reported that quinoline N-oxides and sulfonamides were induced by PhI(OAc) 2 (PIDA) and PPh 3 to synthesize 2-sulfonamideyl quinoline. Nevertheless, a stoichiometric amount of phosphorus reagent was necessary for the successful intermolecular sulfamidation.…”

“…In 2017, Yu and colleagues reported that quinoline N ‐oxides and sulfonamides were induced by PhI(OAc) 2 (PIDA) and PPh 3 to synthesize 2‐sulfonamideyl quinoline. Nevertheless, a stoichiometric amount of phosphorus reagent was necessary for the successful intermolecular sulfamidation . In addition, PhI(OAc) 2 has become one of the most popular research topics in organic synthesis.…”