Reactions of 2-ethyl- and 2-benzyl-1,4-naphthoquinone with N-methylcyclohexylamine

Abstract

2-Ethyl- and 2-benzyl-1,4-naphthoquinone on treatment with N-methylcyclohexylamine in ethanol give 5b,11a-epoxy-5a-ethyl-5a-5b,11a,12a-tetrahydro-12-methyl-12H-dibenzo[b,h]fluorene-5,6,11,13-tetraone (IIIa) and its 5a-benzyl-12-phenyl analogue (IIIb), respectively. Reduction of the epoxides under a variety of conditions eliminates the epoxy-group, and gives various reduction products of the dibenzo[b,h]fluorene-5,13:6,11-quinone system.