Synthesis of substituted dipyrido[3,2- a:2′,3′- c]phenazines and a new heterocyclic dipyrido[3,2- f:2′,3′- h]quinoxalino[2,3- b]quinoxaline

• Published in: Tetrahedron Vol. 64; no. 22; pp. 5410 - 5415
• Main Authors: da Silva Miranda, Fabio, Signori, Aline Maria, Vicente, Juliano, de Souza, Bernardo, Priebe, Jacks Patrick, Szpoganicz, Bruno, Gonçalves, Norberto Sanches, Neves, Ademir
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 26.05.2008; Elsevier
• Subjects: 1,10-Phenanthroline-5,6-dione; B3LYP; Chemistry; Chemistry, Organic; dppz; dpq; Physical Sciences; Science & Technology; Tetraazanaphthacene; B3LYP; Tetraazanaphthacene; dppz; 1,10-Phenanthroline-5,6-dione; dpq; ELECTROPHILICITY; COMPLEXES; 1,2,5-THIADIAZOLES; POSSIBLE DESCRIPTOR; tetraazanaphthacene; 1,10-phenanthroline-5,6-dione; DNA; CHEMISTRY; LIGAND; SPECTRA; ACCEPTOR
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2008.02.097

Three new α,α′-diimine ligands were synthesized based on condensation of 1,10-phenanthroline-5,6-dione with 1,2-phenylenediamine derivatives using different approaches. All compounds were fully characterized by IR, 1H and 13C NMR, UV–visible, and MS spectroscopies. We report the first example of a dipyrido[3,2- f:2′,3′- h]quinoxalino[2,3- b]quinoxaline, which exhibits a strong absorption at 430 nm and an interesting electrochemical behavior. These new molecules may have biological potential and are of synthetic and technological importance. [Display omitted]