The condensation of dehydroacetic acid and 4-hydroxy-6-methylpyran-2-one with primary diamine derivatives such as hydrazine, 1,2-diaminoethane and 1,6-diaminohexane yielded bispyrone and bispyridone derivatives has been reported. The condensation of 4-hydroxy-6-methylpyran-2-one with hydrazine in acetonitrile generated another bispyrazole product but in n-butanol, this reaction afforded the bispyridones. The structures of the synthesized bispyrazoles were examined by spectroscopy and X-ray diffraction analysis, while those of bispyridones were established by spectroscopy data (NMR, mass). Some new complexes were also synthesized in order to show the behaviour of ligands with suitable crystals for X-ray analysis.