Synthesis of oxiranylquinones as new potential bioreductive alkylating agents

1,4-Benzoquinones and 1,4-naphthoquinones carrying oxiranyl substituents have been synthesized as potential bioreduetive alkylating agents. The method presented here involves the syntheses of 1,4-dimethoxybenzalkehydes or 1,4-dimethoxynaphthaldehydes, and conversion of the carbonyl groups into the oxiranyl function using trimethylsulfonium chloride in the presence of powdered sodium hydroxide 1,4-Dimethoxy-2-oxiranyl-benzenes and 1,4-dimethoxy-2-oxiranylnaphthalenes have been oxidized to quinones with silver(II) dipicolinate.