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Abstract: The reaction of N-carboxymethylpyrido[1,2-a]- and pyridazino[1,6-a]benzimidazolium salts with thionyl chloride resulted in an N-C bond fission, yielding the corresponding pyrido [ 1,2-a]-and pyridazino[1,6-a]benzimidazoles. A similar dealkylation process was observed when analogous N-propargylic derivatives were treated with Cu (II) acetate. © 1998 Elsevier Science Ltd. All fights reserved. During a research project focused on the synthesis of new DNA bis-intercalators 1 from pyrido[1,2-a]-and pyridazino[1,6-a]benzimidazolium salts 1by dimerization of the corresponding quaternary heterocycles (Fig. 1), we discovered that an unexpected N-C bond fission process occurred when heteroarylacetic acid