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Convenient Synthesis of a Galacturonic Acid Based Macrocycle with Potential Copper-Complexation Ability

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 C2‐symmetric dimer in different ratios. A preliminary study of the complexation properties of this macrocycle towards CuII cations revealed the formation of cryptates in a 1:1 metal/ligand ratio.
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https://hal.univ-reims.fr/hal-02545898
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Submitted on : Friday, April 17, 2020 - 2:58:09 PM
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Anas Allam, Laurent Dupont, Jean-Bernard Behr, Richard Plantier-Royon. Convenient Synthesis of a Galacturonic Acid Based Macrocycle with Potential Copper-Complexation Ability. European Journal of Organic Chemistry, Wiley-VCH Verlag, 2012, 2012 (4), pp.817-823. ⟨10.1002/ejoc.201101406⟩. ⟨hal-02545898⟩

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