New Synthons for the Synthesis of Lanthanide Containing Macrocyclic Schiff Bases Featuring Substituents Available for Tethering

2,6-Diacetylpyridine substituted with amine or alcohol groups in the 4-position have been prepared from chelidamic acid. The key 4-chloro derivative was synthesized in high yield via a diazo intermediate and was protected as a bis-1,3-dioxane before substitution with various amino alcohol groups. Lanthanide macrocyclic tetra–imine complexes were obtained by a template procedure that leads to stable paramagnetic and/or fluorescent derivatives with anchor groups available for linkage to macromolecules.