Abstract Triethyl phosphite deoxygenation of 2-(2-nitrophenyl) imidazo [1, 2-a][1, 8] naphthyridine (3) led to the C-insertion to give the indoloimidazonaphthyridine 5. Our attempt to promote the N-insertion by blocking the C-3 position failed. Triethyl phosphite deoxygenation of 1-nitroso-2-(4-fluorophenyl) imidazo [1, 2-a][1, 8]-naphthyridine (12) led to the corresponding amine structure (15). Thermolysis and photolysis of 6, 8-dimethyl-2-(2- ...