On the Synthesis of Pyrazino[2, 3-b]phenazine and 1H-Imidazo[4, 5-b]phenazine Derivatives

摘要

Several pyrazino[2, 3-b]phenazine derivatives were prepared by the reaction of 2, 3-diaminophenazine with different 1, 2-diketones. Nucleophilic substitution of 2, 3-dibromomethyl-pyrazino[2, 3-b]phenazine with propanol, morpholine, and potassium thiocyanate gave 1, 3-bis-(propoxymethyl)-pyrazino[2, 3-b]phenazine, 2, 3-bis-(4-morpholinylmethyl)-pyrazino[2, 3-b]phenazine, and 2, 3-bis-(cyanosulfanylmethyl)-pyrazino[2, 3-b]phenazine. 2-Aryl-1H-imidazo[4, 5-b]phenazine derivatives were synthesized by a one-pot reaction of 2, 3-diaminophenazine with different aromatic aldehydes or acids. Reaction of 2, 3-diaminophenazine with acetic anhydride and formic acid afforded 1H-imidazo[4, 5-b]phenazine and 2-methyl-1H-imidazo[4, 5-b]phenazine. Chemical and spectroscopic evidences for the product structures of the new compounds are presented.