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Synthesis of N-(Isoquinolin-1-yl)sulfonamides via Ag2O-catalyzed tandem reaction of ortho-alkynylbenzaldoximes with benchtop stabilized ketenimines

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...

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Hauptverfasser: Hayatgheybi, Sepideh (VerfasserIn) , Khosravi, Hormoz (VerfasserIn) , Zahedian Tejeneki, Hossein (VerfasserIn) , Rominger, Frank (VerfasserIn) , Bijanzadeh, Hamid Reza (VerfasserIn) , Balalaie, Saeed (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: April 14, 2021
In: Organic letters
Year: 2021, Jahrgang: 23, Heft: 9, Pages: 3524-3529
ISSN:1523-7052
DOI:10.1021/acs.orglett.1c00937
Online-Zugang:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1021/acs.orglett.1c00937
Volltext
Verfasserangaben:Sepideh Hayatgheybi, Hormoz Khosravi, Hossein Zahedian Tejeneki, Frank Rominger, Hamid Reza Bijanzadeh, and Saeed Balalaie
Beschreibung
Zusammenfassung: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.
Beschreibung:Im Text ist "2" tiefgestellt
Gesehen am 01.03.2022
Beschreibung:Online Resource
ISSN:1523-7052
DOI:10.1021/acs.orglett.1c00937

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