Synthesis of Oligopyridinic Scaffolds from Amido Substituted Phenyl Rings for Extended Hydrogen Bonding

Guillaume Pickaert; Raymond Ziessel

doi:10.1055/s-2004-831241

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Synthesis of Oligopyridinic Scaffolds from Amido Substituted Phenyl Rings for Extended Hydrogen Bonding

Guillaume Pickaert, Raymond Ziessel*
Laboratoire de Chimie Moléculaire, Associé au CNRS, Ecole de Chimie, Polymères, Matériaux de Strasbourg (ECPM), 25 rue Becquerel, 67087 Strasbourg, Cedex 02, France
Fax: +33(390)242689; e-Mail: ziessel@chimie.u-strasbg.fr;

Abstract

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Abstract

A series of phenanthroline, terpyridine and pyridino-oxazoline ligands combining a 4-methyl-3,5-diacylaminophenyl platform and two dialkoxyphenyl groups has been prepared by a linear multistep protocol. The synthetic potential of 4-methyl-3,5-(diacylaminodialkoxyphenyl)benzoic acids was assessed by the construction, in a single step, of the chelating fragments. The grafting of these nitrogen-based groups is realized by the use of EDC·HCl and DMAP reagents under mild conditions. The synthetic methods reported herein provide a practical approach to the rational design of ligands bearing various kinds of functionalities such as the ester and amido linkages as well as the paraffin chains. A significant merit of this method is that it allows the introduction of the 4-methyl-3,5-diacylaminophenyl platform onto the oligopyridinic framework at the end of the synthetic protocol.

Keywords

phenanthroline - terpyridine - pyridino-oxazoline - amides - hydrogen bonds

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References

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