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Synthesis and anion binding behaviour of diamide derivatives of pyrrole-2,5-diacetic acid

By Rongqing Li, Louise S. Evans, David S. Larsen, Philip A. Gale and Sally Brooker

Abstract

Four examples of bis-amidopyrrole derivatives of pyrrole-2,5-diacetic acid have been prepared. The reaction of diethyl pyrrole-2,5-diacetate with a large excess (24 equiv.) of N,N-dimethylethylenediamine gave N,N0-bis(2-dimethylaminoethyl)-1H-pyrrole-2,5-diacetamide (1). Three further examples, N,N0-bis[2-(2-pyridyl)ethyl]-1H-pyrrole-2,5-diacetamide (2), N,N-bis(2-pyridylmethyl)-1H-pyrrole-2,5-diacetamide (3) and N,N0-dibenzyl-1H-pyrrole-2,5-diacetamide (4), were prepared in a one pot procedure by converting pyrrole-2,5-diacetic acid into the N-hydroxysuccinimide ester and then reacting this with four equivalents of the appropriate amine, 2-(2-aminoethyl)pyridine, 2-aminomethylpyridine or benzylamine, respectively. Compounds 1–4 are shown to be effective anion receptors in acetonitrile-d3 solution, with comparable binding affinities to those found for simple pyrrole-2,5-dicarboxamides, despite possessing a more flexible hydrogen bonding array

Topics: QD
Year: 2004
OAI identifier: oai:eprints.soton.ac.uk:15723
Provided by: e-Prints Soton
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