title: 2-Aminobenzenesulfonamide-Containing Cyclononyne as Adjustable Click Reagent for Strain-Promoted Azide-Alkyne Cycloaddition.
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.
authors.affiliation: Hokkaido Pharmaceutical University School of Pharmacy , 7-15-4-1 Maeda Teine Sapporo, Hokkaido 006-8590, Japan.
authors.forename: Kyosuke
authors.identifier: 0000-0003-2415-2685
authors.initials: K
authors.lastname: Kaneda
authors.affiliation: Hokkaido Pharmaceutical University School of Pharmacy , 7-15-4-1 Maeda Teine Sapporo, Hokkaido 006-8590, Japan.
authors.forename: Risa
authors.initials: R
authors.lastname: Naruse
authors.affiliation: Hokkaido Pharmaceutical University School of Pharmacy , 7-15-4-1 Maeda Teine Sapporo, Hokkaido 006-8590, Japan.
authors.forename: Syota
authors.initials: S
authors.lastname: Yamamoto