Abstract : We present herein an extension of the TDAE strategy using original heterocyclic carbaldehyde as electrophiles. We also evaluate the influence of the presence of nitro group on the reactivity. The TDAE-initiated reactions of various halomethyl and gem-dihalomethyl derivatives with non-nitrated carbaldehyde 1 or 2 formed the expected products accompagnied by original rearranged products while the presence of a nitro group just like the carbaldehyde 21 furnished only the expected products in good yields.