Studies on polycyclic fluoroazaarenes: Synthesis of trans-9-fluoro-and -11-fluoro 3,4-dihydroxy-3,4-dihydrobenz[c]acridines as potential proximate carcinogenic metabolites of fluorobenz[c]-acridine

Stereoselective syntheses of the title compounds trans-9-fluoro-3,4-dihydroxy-3,4-dihydrobenz[c]acridine 1a and trans-11-fluoro-3,4-dihydroxy-3,4-dihydrobenz[c]acridine 1b, as proximate carcinogenic metabolites of 9- and 11-fluorobenz[c]acridines, respectively, are described. In order to compare mutagenic activities with their parent fluoroazaarenes, 9-fluorobenz[c]acridine 2a and 11-fluorobenz[c]acridine 2b, have also been synthesised. The dihydrodiols were obtained by the stereoselective reduction of o-quinones, which in turn were synthesised by following the protocol of functional group transformation of methoxy→phenol→o-quinone.