1,2,3-triHeterocycle-substituted aziridines were prepared by coupling of (alpha-chioroalkyl) oxazolinyllithium compounds with diheteroaryl imines. The trapping by different electrophiles of the corresponding aziridinyl anions, generated by treatment with strong bases, was investigated. The stereoselectivity of the synthesis and the functionalization reactions was studied highlighting the different stabilizing effects of the heterocycle substituents.