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.
|Original language||English (US)|
|Number of pages||6|
|Journal||Journal of the Chemical Society. Perkin Transactions 1|
|State||Published - Jan 1 2001|
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