Optically active pyridine‐2,6‐bis(4‐azidomethyloxazoline) was prepared by starting from L‐serine and pyridine 2,6‐dicarboxylic acid. Reduction of the azide moieties gave pyridine‐2,6‐bis(4‐aminomethyloxazoline), which was not a stable compound, but readily underwent a ring‐transforming rearrangement to furnish the pyridine‐2,6‐bis(4‐hydroxymethylimidazoline). After Boc protection of the amidine functionalities, this compound could be further converted into the pyridine‐2,6‐bis(4‐aminomethylimidazoline) via the corresponding bis(azidomethyl) compound. The azide functions of the bis(oxazoline) and the bis(imidazoline) intermediate products could also be further derivatized with an alkyne to give triazoles or through aza‐Wittig reactions with benzaldehyde to give imines.