2,6,9-Triazabicyclo[3.3.1]nonanes as overlooked amino-modification products by acrolein

Abstract

The reaction of several primary amines with acrolein smoothly provided the corresponding 2,6,9-triazabicyclo[3.3.1]nonanes through a formal [4 + 4] reaction of the intermediary unsaturated imines. The reactivity profiles in aqueous media and the results from cytotoxic activity assays suggested that the caged products may be relevant in biological systems and may contribute to the mechanisms underlying the oxidative stress response to acrolein.