Synthesis of <i>N</i>-(Isoquinolin-1-yl)sulfonamides via Ag<sub>2</sub>O-Catalyzed Tandem Reaction of <i>ortho</i>-Alkynylbenzaldoximes with Benchtop Stabilized Ketenimines
Sepideh Hayatgheybi, Hormoz Khosravi, Hossein Zahedian Tejeneki, Frank Röminger, Hamid Reza Bijanzadeh, Saeed Balalaie
Abstract
In this project, a moderately efficient approach to multisubstituted N-(isoquinolin-1-yl)sulfonamide derivatives was illustrated, utilizing ortho-alkynylbenzaldoximes and zwitterionic ketenimine salts in a tandem reaction catalyzed by silver oxide. The oxophilicity of Ag2O, along with its nature as Lewis acid, pave the way for a smooth [3 + 2] cycloaddition between isoquinoline N-oxides and ketenimine species, which is a key step in this reaction. DFT calculation suggests that 1,3-dipolar cycloaddition of nitrone and ketenimine proceeds through a selective stepwise mechanism.
Topics & Concepts
KetenimineChemistryCycloadditionCatalysisTandemIsoquinolineSulfonamideNitroneCombinatorial chemistryLewis acids and basesStepwise reactionMedicinal chemistryStereochemistryOrganic chemistryReaction rate constantKineticsPhysicsQuantum mechanicsMaterials scienceComposite materialOrder of reactionClick Chemistry and ApplicationsSynthesis and Catalytic ReactionsCatalytic Alkyne Reactions