Synthesis and evaluation of 3-acyltetronic acid-containing metal complexing agents

Potential metal chelators containing one or several acyltetronic acid moieties were prepared from cyclic or acyclic amines and polyamines, and from bis(phenols) by reaction with 1–4 equiv of 3-bromoacetyltetronic acid in the presence of potassium carbonate. The affinity constants of the chelating agents for toxic metallic cations Cd2+, Cs+, and Pb2+ and for dimethylarsinic acid were measured, at pH 7.5 and 9.3. Compound 4, an acyclic triamine containing four acyltetronic moieties, was found to complex efficiently all the tested species.