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Convenient Synthesis of a Galacturonic Acid Based Macrocycle with Potential Copper‐Complexation Ability
Author(s) -
Allam Anas,
Dupont Laurent,
Behr JeanBernard,
PlantierRoyon Richard
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201101406
Subject(s) - chemistry , intramolecular force , cycloaddition , ring (chemistry) , amide , dimer , triazole , copper , azide , ligand (biochemistry) , combinatorial chemistry , polymer chemistry , medicinal chemistry , stereochemistry , organic chemistry , catalysis , receptor , biochemistry
Abstract A convenient approach to the construction of a galacturonic acid based macrocycle containing an amide group and a triazole ring has been achieved. The key step relies on the efficient formation of a 16‐membered ring by a copper‐catalysed intramolecular cycloaddition reaction applied to analkyne‐azide galacturonate. Depending on the reaction conditions, the outcome of the 1,3‐dipolar cycloaddition varied; the expected intramolecular 1,4‐triazole was obtained as well as a C 2 ‐symmetric dimer in different ratios. A preliminary study of the complexation properties of this macrocycle towards Cu II cations revealed the formation of cryptates in a 1:1 metal/ligand ratio.