Synthesis of arene oxide and trans-dihydrodiol metabolites of quinoline

Abstract

Racemic samples of 5,6-epoxy-5,6-dihydroquinoline (2)(quinoline 5,6-oxide) and 7,8-epoxy-7,8-dihydroquinoline (4)(quinoline 7,8-oxide) have been synthesised by two methods from the corresponding dihydroquinoline precursors. trans-5,6-Dihydroquinoline-5,6-diol (3) and trans-7,8-dihydroquinoline-7,8-diol (5) were obtained both by multi-step synthetic routes from the corresponding dihydroquinolines and by the direct base-catalysed hydration of the corresponding arene oxides (2) and (4).