Synthesis of Dihydrodiols and Diol Epoxides of Dibenzacridine

Article abstract of DOI:10.1021/jo00363a008

trans-1,2-Dihydroxy-1,2-dihydrodibenzacridine (5), trans-3,4-dihydroxy-3,4-dihydrodibenzacridine (6), trans-8,9-dihydroxy-8,9-dihydrodibenzacridine (7), 3α,4β-dihydroxy-1α,2α-epoxy-1,2,3,4-tetrahydrodibenzacridine (9), and 3α,4β-dihydroxy-1β,2β-epoxy-1,2,3,4-tetrahydrodibenzacridine (10), which are potentially proximate and ultimate carcinogens of dibenzacridine (1), are synthesized from a common intermediate 8,9,10,11-tetrahydrodibenzacridine (13).The Birch reduction of 13 produced an intermediate which has been used in preparing 5 and 6.However, the bromination of 13 followed by dehydrobromination resulted in a mixture of isomeric alkenes which was successfully converted to 7. 1H NMR, UV, and mass spectra of dibenzacridine derivatives are reported.