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Synthesis 2006(9): 1504-1512  
DOI: 10.1055/s-2006-926439
PAPER
© Georg Thieme Verlag Stuttgart · New York

New Ditopic and Tripodal 1,2,4-Triazole- and Tetrazole-Based Ligands for Coordination Chemistry

Yves Bolanda, Pascale Hertsensa, Jacqueline Marchand-Brynaertb, Yann Garcia*a
a Unité de Chimie des Matériaux Inorganiques et Organiques, Département de Chimie, Faculté des Sciences, Université catholique de Louvain­, Place L. Pasteur 1, 1348 Louvain-la-Neuve, Belgium
b Unité de Chimie Organique et Médicinale, Département de Chimie, Faculté des Sciences, Université catholique de Louvain, Place L. Pasteur 1, 1348 Louvain-la-Neuve, Belgium
Fax: +32(10)472831; e-Mail: garcia@chim.ucl.ac.be;
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Publication History

Received 12 October 2005
Publication Date:
11 April 2006 (online)

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Abstract

The practical synthesis of two new classes of polytopic azole-based ligands is reported. The synthesis of the precursor amines was achieved by substitution of a leaving group by an azide followed by reduction with triphenylphosphine and water. Another efficient method employs a Mitsunobu coupling with phthalimide allowing the conversion of a primary alcohol into a primary amine. The triazole and tetrazole were obtained by cyclization of these amine precursors. The first family consisted of ditopic ligands containing both 1-R-tetrazole and 4-R-1,2,4-triazole moieties linked by an alkyl spacer, while the second consists of branched ligands with three azole cycles linked to a benzene core through ether bonds. Both classes are suitable for building multidimensional polynuclear coordination assemblies and for the observation of thermal spin state crossover behavior with iron(II) ions.

Key words

ligands - heterocycles - Mitsunobu reaction - coordination chemistry

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