When attempting to extend the Zn(OTf)₂-catalyzed hydrazination of propargylic amides (en route to Fischer indoles) to alkanoic propargylamides, it was discovered that after the initial hydrazination event, the respective N-anilinoimidazoles are obtained. The use of stoichiometric ZnCl₂ as the promoter still gave the Fischer indole product. The unexpected reaction outcome was attributed to the overly high electrophilicity of the alkanoic carboxamide carbon atom.