1.
J Org Chem
; 82(5): 2386-2398, 2017 03 03.
Artigo
em Inglês
| MEDLINE
| ID: mdl-28225627
RESUMO
The cis-directing effect of the 1,2,3-triazolium-type side chain was studied on dimeric peptoid models with various patterns: αα, αß, ßα and ßß. Low influences of the sequence and of the solvent were observed, the cis conformation of the amide carrying the triazolium ranging from 83 to 94% in proportion. The synthesis of peptoid homooligomers with four or eight pendant 1,2,3-triazolium side chains is described. α-, ß- and α,ß-peptoids carrying propargyl groups were subjected to CuAAC reaction using alkyl azides, and the resulting triazoles were quaternized providing well-defined multitriazolium platforms. The influence of the counteranion (PF6-, BF4- or I-) on the conformation was also studied.