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Synthesis 2008(1): 79-86
DOI: 10.1055/s-2007-990904
DOI: 10.1055/s-2007-990904
PAPER
© Georg Thieme Verlag Stuttgart · New York
A General One-Step Synthesis of Multidentate (Pyridylalkyl)amines from Mono-, Bis-, Tris- and Tetrakis(bromomethyl)benzenes: Potential Ligands for Supramolecular Assembly
Further Information
Received
9 July 2007
Publication Date:
15 November 2007 (online)
Publication History
Publication Date:
15 November 2007 (online)
Abstract
The synthesis of new multidentate nitrogen-containing ligands is of ongoing interest. In this report, the one-step syntheses of a series of (pyridylalkyl)amine derivatives is described. The reported compounds contain both pyridine rings and sp3-hybridized nitrogen as potential donor sites. The general synthetic method involves a room temperature reaction of mono-, bis-, tris-, or tetrakis(bromomethyl)benzenes with an excess of (pyridylmethyl)amine in tetrahydrofuran. The products can be purified by distillation, chromatography or recrystallization and are obtained in fair to good yields. The advantages of this synthetic method are the procedural simplicity and the ready availability of the starting materials. The applicability of these compounds in supramolecular chemistry is demonstrated by the reaction of two of the described ligands with silver(I) salts.
Key words
pyridines - amines - alkylations - ligands - supramolecular chemistry
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60CCDC 254148 (14), 282437 (19) and 648447 (20) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.