Reaction of imines of aminoanthraquinones with formaldehyde and alkenes

Article abstract of DOI:10.1016/0040-4020(95)00270-I

By reaction of mono- and di-aminoanthraquinones with formaldehyde and diverse electron rich alkenes in acetonitrile in the presence of trifluoroacetic acid cyclocondensation affords a series of tetrahydroquinolines. The resulting tetra-, penta- and hepta-cyclic products all contain the anthraquinone sub-structure. Aspects of regio- and stereo-selectivity are discussed and the potential of this series of aminoanthraquinones for metal ion chelation and binding in DNA are noted.