“ N‐CH ₂ ‐C ” Linked Carbohydrate‐Based Hybrid Short Triazolamers and Oligotriazoles Designed With 1,4‐Disubstituted 1,2,3‐triazolyl, 1,5‐Disubstituted 1,2,3‐triazolyl and/or 1,4,5‐Trisubstituted 1,2,3‐triazolyl Moieties: Syntheses Using Huisgen, Click, and Vinyl Sulfone Chemistry

In order to develop a strategy for the synthesis 1,2,3‐triazole‐based oligomers and triazolamers where monomeric triazole moieties are linked by “ N‐CH 2 ‐C ” units, copper‐catalyzed azide alkyne cycloaddition method, vinyl sulfone‐based eliminative azide‐olefinic cycloaddition route and Huisgen's strategy of triazole formation at an elevated temperature were combined in a step‐wise and well‐planned manner. The monomeric blocks, namely 1,4‐disubstituted 1,2,3‐triazole, 1,5‐disubstituted 1,2,3‐triazole, and 1,4,5‐trisubstituted 1,2,3‐triazole units decorated with CH 2 N 3 functional group at C4, C5, and C4‐C5, respectively, were synthesized using three different reactions mentioned above. The 1,4‐disubstituted 1,2,3‐triazole monomeric block provides the option for the construction of 1,2,3‐triazole units leading to the formation of [1,4]‐ N‐CH 2 ‐C ‐[1,4], [1,4]‐ N‐CH 2 ‐C ‐[1,5] and [1,4]‐ N‐CH 2 ‐C ‐[1,4,5] dimeric blocks. Similarly, 1,5‐disubstituted 1,2,3‐triazole monomeric block afforded [1,5]‐ N‐CH 2 ‐C ‐[1,4], [1,5]‐ N‐CH 2 ‐C ‐[1,5] and [1,5]‐ N‐CH 2 ‐C ‐[1,4,5] dimeric blocks whereas 1,4,5‐trisubstituted 1,2,3‐triazole monomeric block generated [1,4,5]‐( N‐CH 2 ‐C) 2 ‐[1,4][1,4], [1,4,5]‐( N‐CH 2 ‐C) 2 ‐[1,5][1,5] and [1,4,5]‐( N‐CH 2 ‐C) 2 ‐[1,4,5][1,4,5] branched trimeric blocks. Thereafter, the repetition of three triazole‐forming reactions lead to several homo/hetero tris and tetrakis‐ branched oligotriazoles and triazolamers. In most of the cases, the “N” and “C” terminals are modified with sugar and phenyl residues (two different groups), respectively, although examples of both “N” and “C” terminal ends with sugar component (similar groups) are also generated.