Innovative Methodologies for the N-Protection of N-Alkylimidazole Groups:  Application to the First Synthesis of a Water-Soluble Calix[6]arene Presenting Three Ammonium Substituents at the Large Rim and Three Neutral N-Donors at the Small Rim

The first synthesis of a cationic amphiphile calixarene ligand, which bears three neutral imidazole donors on one side of the hydrophobic cone and three quaternary ammonium substituents on the other side, is reported. The synthetic strategy relies on two key steps:  (i) the “small rim-directed” sele...

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Bibliographic Details
Published in:Organic letters 2007-08, Vol.9 (17), p.3271-3274
Main Authors: Coquière, David, Marrot, Jérôme, Reinaud, Olivia
Format: Article
Language:English
Subjects:
Calixarenes - chemical synthesis
Methods
Phenols
Quaternary Ammonium Compounds
Solubility
Water
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Summary:The first synthesis of a cationic amphiphile calixarene ligand, which bears three neutral imidazole donors on one side of the hydrophobic cone and three quaternary ammonium substituents on the other side, is reported. The synthetic strategy relies on two key steps:  (i) the “small rim-directed” selective ipso-nitration at the large rim and (ii) a protection−deprotection sequence of the N-alkylimidazole groups, for which two equally efficient novel methods (coordination to Zn(II) or to a cyanoborane) are presented.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol071208t