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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| Main Authors: | , , , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
April 14, 2021
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| In: |
Organic letters
Year: 2021, Volume: 23, Issue: 9, Pages: 3524-3529 |
| ISSN: | 1523-7052 |
| DOI: | 10.1021/acs.orglett.1c00937 |
| Online Access: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1021/acs.orglett.1c00937
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| Author Notes: | Sepideh Hayatgheybi, Hormoz Khosravi, Hossein Zahedian Tejeneki, Frank Rominger, Hamid Reza Bijanzadeh, and Saeed Balalaie |
| Summary: | 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. |
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| Item Description: | Im Text ist "2" tiefgestellt Gesehen am 01.03.2022 |
| Physical Description: | Online Resource |
| ISSN: | 1523-7052 |
| DOI: | 10.1021/acs.orglett.1c00937 |