Two synthetic pathways to substituted hexahydroimidazo[1,2-a]pyridines, which may serve as precursors of aza-alkaloids, were investigated. The first involves the condensation of a bisnucleophilic enediaminoester and a biselectrophile. The second involves attachment to nitrogen of the carbon chain skeleton required to form the six-memberd ring, before formation of the enediaminoester. Several substituted hexahydroimidazo[1,2- a]pyridines were synthesized via these two approaches.