期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2012, 期 4, 页码 817-823出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201101406
关键词
Click chemistry; Macrocycles; Nitrogen heterocycles; Copper; Carbohydrates
资金
- Region Champagne-Ardenne
- Centre National de la Recherche Scientifique (CNRS)
- Institut National de la Recherche Agronomique (INRA) [RDR1 CP2D]
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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