Novel tricyclic dipyridoimidazole derivatives can be readily synthesised in one pot processes from various highly fluorinated pyridine systems such as pentafluoropyridine and relatively nucleophilic 2-aminopyridine derivatives. Further nucleophilic aromatic substitution reactions of the novel tricyclic scaffolds allow the regioselective synthesis of various nitrogen, oxygen, carbon and sulfur-functionalised dipyridoimidazole products. (C) 2009 Elsevier Ltd. All rights reserved.