Synthesis of oxaziridinylquinones and oxaziridinylazines as potential antitumor agents

Abstract 1,4‐Benzoquinones, 1,4‐naphthoquinones, as well as pyridines and quinolines having 2‐alkyloxaziridinyl substituents were synthesized. The method involves formation of aldimines and their oxidation to oxaziridines. 1,4‐Dimethoxyarenes bearing oxaziridinyl substituents were converted into the corresponding quinones with silver(II) dipicolinate. Some of the oxaziridinylquinones and ‐azines exhibit activity against KB cells, and the structure‐activity relationship is discussed in terms of the current theory of biologically activated alkylating agents.