By reaction of mono- and di-aminoanthraquinones with formaldehyde and
diverse electron rich alkenes in acetonitrile in the presence of trifl
uoroacetic acid cyclocondensation affords a series of tetrahydroquinol
ines. The resulting tetra-, penta- and hepta-cyclic products all conta
in the anthraquinone sub-structure. Aspects of regio- curd stereo-sele
ctivity are discussed and the potential of this series of aminoanthraq
uinones for metal ion chelation and binding in DNA are noted.