One-pot synthesis of disulfide-linked N-sulfonylazetidin-2-imines via a copper-catalyzed multicomponent cascade reaction

One-pot synthesis of disulfide-linked N-sulfonylazetidin-2-imines via a copper-catalyzed multicomponent cascade reaction

A copper-catalyzed, three-component reaction between a sulfonyl azide, an alkyne, and a 2-aminothiophenol derived Schiff base is reported. This novel one-pot procedure involves a click reaction, a formal [2+2] cycloaddition, and S–S coupling, therefore, providing a unique method for the synthesis of...

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Veröffentlicht in:Tetrahedron 2013-11, Vol.69 (47), p.10134-10138
Hauptverfasser: Shang, Yongjia, Liao, Kaisheng, He, Xinwei, Hu, Jinsong
Format: Artikel
Sprache:eng
Schlagworte:
Alkynes
Cascade chemical reactions
Coupling reaction
Cycloaddition
Joining
Ketenimines
Multicomponent reaction
N-Sulfonylazetidinimines
Schiff bases
Synthesis
Tetrahedrons
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Zusammenfassung:A copper-catalyzed, three-component reaction between a sulfonyl azide, an alkyne, and a 2-aminothiophenol derived Schiff base is reported. This novel one-pot procedure involves a click reaction, a formal [2+2] cycloaddition, and S–S coupling, therefore, providing a unique method for the synthesis of novel disulfide-linked N-sulfonylazetidin-2-imines under mild conditions. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2013.09.033