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Updated: Jun 15, 2026

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
"Click" synthesis of nonsymmetrical bis(1,2,3-triazoles)
Jesus M Aizpurua1, Itxaso Azcune, Raluca M Fratila
1Departamento de Química Orgánica-I, Universidad del País Vasco, Joxe Mari Korta R&D Center, Avda Tolosa-72, 20018 San Sebastián, Spain. jesusmaria.aizpurua@ehu.es
Abstract:
Unsymmetrically 1,1'-disubstituted 4,4'-bis-1H-1,2,3-triazoles 4 have been prepared from 4-ethynyl-1,2,3-triazoles 5 and azides. Following a "double-click" strategy, two complementary approaches were implemented for the preparation of the key 4-ethynyltriazole intermediates 5: (a) the stepwise Swern oxidation/Ohira-Bestman alkynylation of readily available 4-hydroxymethyl-1,2,3-triazoles 8 and (b) the stepwise cycloaddition of TMS-1,4-butadiyne 9. The method is highlighted by its compatibility with orthogonally protected and functionalized saccharide-peptide hybrids and its ability to be extended to the trisubstituted counterparts 12.
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