Baylis–Hillman-derived N,N′-disubstituted piperazines: structural and preliminary computational studies

Exploratory studies towards the preparation of potential HIV-1 protease and integrase inhibitors have led to the synthesis of Baylis–Hillman-derived N,N′-disubstituted piperazines. X-ray crystallographic, computer modelling and NMR techniques have been used to elucidate questions concerning configurational preferences, reaction pathways and the apparent difference in susceptibility towards aza-Michael reactions exhibited by methyl acrylate and methyl vinyl ketone (MVK) derived Baylis–Hillman substrates.