Synthesis and regioselective functionalization of piperazin-2-ones based on Phe-Gly pseudodipeptides

Abstract

The synthesis of 1,4-unsubstituted piperazin-2-ones by one-pot reductive cyclization of Pheο[CH(CN)NH]Gly pseudodipeptides is described. Studies on the reactivity of the piperazin-2-one ring showed a higher reactivity at the N4 position than at the N1 position. The stepwise regioselective functionalization of piperazin-2-one derivatives showed great potential for molecular diversity generation. An easy methodology for the synthesis of the piperazin-2-ones by one-pot reductive cyclization of Pheο[CH(CN)NH]Gly pseudodipeptides is described. Study of the reactivity of the piperazin-2-one ring has shown that regioselective functionalization at the N1 and N4 positions is possible, and hence great potential for molecular diversity generation.