Fine tuning reactivity: synthesis and isolation of 1,2,3,12b-tetrahydroimidazo[1,2-f]phenanthridines.
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.
Richmond
Craig J
CJ
WestCHEM, Department of Chemistry, University of Glasgow, Glasgow G12 8QQ, United Kingdom.
Eadie
Roslyn M
RM
Parenty
Alexis D C
AD
Cronin
Leroy
L
D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D010617:Phenanthridines / Q000138:chemical synthesis* / Q000302:isolation & purification; D013055:Spectrophotometry, Infrared
D010617:Phenanthridines