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In this work we report the Pd-catalyzed synthesis of macrocyclic N,O- and N-ligands possessing heteroaromatic units suitable for fluorescent detection of toxic metal ions. Quinoline, 1,10-phenanthroline and 2,3-diphenylquinoxaline derivatives were prepared according the cyclization reaction in yields up to 35%. Moreover, the 1,10-phenanthroline-containing ditopic ligands were transformed into corresponding luminescent Ru(II) complexes.