Nitration of pre-assembled Troger's base analogs

The presence of a nitro functional group on an aromatic ring provides a valuable entry point for the introduction of other functionalities such as amine, diazo, hydroxyl, nitrite etc. In our present study we have used urea nitrate and potassium nitrate to introduce nitro groups onto several Tröger's base compounds, post-assembly of the skeleton. We have also examined the regiochemistry of the reactions in the presence of different nitrating agents and the effect of R groups with differing activating effects These reactions constitute the first examples of direct introduction of the nitro functional group on pre-assembled Tröger’s base analogs.