I. Lázár
1999
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7
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Abstract
Near quantitative synthesis of 1,4,8-tris(carbamoylmethyl)-1,4,8,11-tetraazacyclotetradecane hydroiodide (1) has been achieved by reacting the parent macrocycle 1,4,8,11-tetraazacyclotetradecane (cyclam) with iodoacetamide in acetone in the presence of diisopropylethylamine as a base. The reaction stops at the trisubstituted stage even in the presence of a large excess of the reactants. This process represents the first example of a solubility controlled regioselective synthesis of a polyazamacrocyclic complexing agent; the driving force is the exceptionally low solubility of 1 was hydrolyzed in acidic medium to the corresponding acetate derivative 1,4,8-tris(car☐ylmethyl)-1,4,8,11-tetraazacyclotetradecane (2) in high yield.