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Synthesis 2009(20): 3419-3426  
DOI: 10.1055/s-0029-1216968
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis and Functional Group Transformations of Tris(pyrazol-1-yl)meth­ane (Tpm) and -ethane (Tpe) Derivatives for the Preparation of Sterically Hindered Chelating Macrobicycles

Leyong Wang, Clément Michelin, Jean-Claude Chambron*
Institut de Chimie Moléculaire de l’Université de Bourgogne (ICMUB, UMR CNRS n˚ 5260), 9 avenue Alain Savary, BP 47870, 21078 Dijon cedex, France
Fax: +33(3)80396117; e-Mail: jean-claude.chambron@u-bourgogne.fr;
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Publication History

Received 19 May 2009
Publication Date:
28 August 2009 (online)

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Abstract

Tris(pyrazol-1-yl)methane (Tpm) and -ethane (Tpe) chelate derivatives bearing meta-benzonitrile groups in the position ortho to the coordinating nitrogen atom have been prepared from 3-(1H-pyrazol-3-yl)benzonitrile, and subjected to functional group transformations leading to the corresponding benzylthiol-substituted derivatives. The Tpe analogue was reacted with 1,3,5-tribromomethylbenzene in basic conditions to afford the Tpe-incorporating macrobicycle 2 in 40% yield.

Key words

chelates - heterocycles - ligands - macrobicycles - pyrazoles

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1

Current address: Key Laboratory of Mesoscopic Chemistry of Ministry of Education and School of Chemistry and Chemical Engineering, Nanjing University, 210093 Nanjing, P. R. of China.