Convenient methods for the preparation of (het)aryl-substituted derivatives of 1-azatriptycene, including the cyclopentene-condensed analog, were proposed using the "1,2,4-triazine" methodology. The 1,2,4-triazatriptycene derivatives were synthesized for the first time. New original ligands of the 2,2'-bipyridine series are among the synthesized compounds.