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2-Aminobenzenesulfonamide-Containing Cyclononyne as Adjustable Click Reagent for Strain-Promoted Azide-Alkyne
Kyosuke Kaneda1, Risa Naruse1, Syota Yamamoto1
1Hokkaido Pharmaceutical University School of Pharmacy , 7-15-4-1 Maeda Teine Sapporo, Hokkaido 006-8590, Japan.
Abstract:
The synthesis of 2-aminobenzenesulfonamide-containing cyclononyne (ABSACN), starting from 2-nitrobenzenesulfonamide and but-2-yne-1,4-diol via Mitsunobu and Nicholas reactions, is described for the development of an adjustable alkyne reagent in click reactions. In a strain-promoted azide-alkyne cycloaddition (SPAAC) reaction, the reactivity of the alkyne is controlled by introducing various N-functionalities. The structure-reactivity relationship is found to be influenced by a transannular hydrogen bond between amino and sulfonyl groups.
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