title: Fine tuning reactivity: synthesis and isolation of 1,2,3,12b-tetrahydroimidazo[1,2-f]phenanthridines.
abstract: A facile route for the synthesis and isolation of 1,2,3,12b-tetrahydroimidazo[1,2-f]phenanthridines (TIPs) has been developed. The heterocycle is a reactive intermediate in the three-step cascade synthesis of 2,3-dihydro-1H-imidazo[1,2-f]phenanthridinium cations (DIPs), a biologically active DNA intercalating framework; however, the intermediate has previously only been characterized in situ. Derivatization of the structure at the imidazo-N position controls the reactivity of the intermediate with respect to electronic potential and pK(a) allowing isolation of a selection of TIP structures. Correlations between these parameters and reaction outcome have been made, and other influences such as steric and solvent effects have also been investigated.
authors.affiliation: WestCHEM, Department of Chemistry, University of Glasgow, Glasgow G12 8QQ, United Kingdom.
authors.forename: Craig J
authors.initials: CJ
authors.lastname: Richmond
authors.forename: Roslyn M
authors.initials: RM
authors.lastname: Eadie
authors.forename: Alexis D C
authors.initials: AD
authors.lastname: Parenty
authors.forename: Leroy
authors.initials: L
authors.lastname: Cronin
mesh_terms: D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D010617:Phenanthridines / Q000138:chemical synthesis* / Q000302:isolation & purification; D013055:Spectrophotometry, Infrared
chemical_list: D010617:Phenanthridines