Convenient Synthesis of a Galacturonic Acid Based Macrocycle with Potential Copper‐Complexation Ability | Zendy

Allam Anas | Zendy; Dupont Laurent | Zendy; Behr JeanBernard | Zendy; PlantierRoyon Richard | Zendy

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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

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.

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