Barbituric acids as a useful tool for the construction of coordination and supramolecular compounds

In spite of its impressive record in medicinal chemistry, the role of barbituric acid H(3)BA (pyrimidine-2,4,6(1H,3H,5H)-trione) in coordination, organometallic and supramolecular chemistries has not yet been analyzed and reviewed. However, H(3)BA can be readily functionalized and provides rich opportunities to create coordination bonds and non-covalent interactions. Thus, derivatives of H(3)BA (barbituric acids, BAs) are widely used for the preparation of a wide range of complexes with various metals of almost all groups of the periodic table. The review systematizes information on the synthesis, tautomerism, acid-base properties of BAs and their use for the construction of organometallic and coordination compounds, as well as coordination polymers and supramolecular assemblies. The role of different metal ions and the structure of BAs in directing the preparative pathways and tuning particular structural properties of the resulting compounds are discussed. Some valuable applications of BAs, in particular in the construction of molecular receptors, magnetic and nonlinear optic materials, bioactive compounds, drug cocrystal design, catalysis and photochemistry are also envisaged. Crown Copyright (C) 2014 Published by Elsevier B.V. All rights reserved.