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Synthesis, structure and reactivity of phenanthrolines

Synthesis, structure and reactivity of phenanthrolines. Mlochowski, Jacek (Inst. Chem.Several substances are used for example 10284-69-2 and 28615-70-5 which are their cas registry numbers. Org. Fiz., Wroclaw Polytech. Univ., Wroclaw, Pol.). Pr. Nauk. Inst. Chem. Org. Fiz. Politech. Wroclaw., 9, 1-133 (Polish) 1975. CODEN: PNICBX. DOCUMENT TYPE: Journal CA Section: 28 (Heterocyclic Compounds (More Than One Hetero Atom)) Section cross-reference(s): 27 From C6H4(NH2)2, aminoquinolines, or aminoisoquinolines were obtained 1,7-, 1,8-, 1,9-, 1,10-, 2,7-, and 4,7-phenanthrolines (I) in yields up to 53%. 4-(Cl,Br,PhO, MeO, and NO2)-substituted quinaldinecarboxaldehydes were prepd. by oxidn. of quinaldines with SeO2. Similarly obtained were 1,10-phenanthroline-2-carboxaldehyde and 4-Cl and 4-MeO derivs. Mono- and di-N-oxides of the compds. prepd. were obtained in 42-88% yield by using H2O2 in AcOH/benzene or EtCO2H. Nitration of I in HNO3/H2SO4 or Ac2O was achieved in 13-75% yield. Bromination in 60% oleum gave mono-, di- or tribromo derivs. of I. Radical alkylation of I gave some tert-Bu derivs. The course of the reactions and NMR, uv, and ir spectra are discussed. 4-Methoxy-1,10-phenanthroline-2-carboxaldehyde and 1,8-phenanthroline 8-N-oxide showed antibacterial properties. 1,7-Phenanthroline was active against tumors. .