A new synthetic approach to the imidazo[1,5-a]imidazole-2-one scaffold and effective functionalization through Suzuki-Miyaura cross coupling reactionsElectronic supplementary information (ESI) available. See DOI: 10.1039/c5ra25520a

We report herein a synthetic pathway to new 7-bromo-1-(4-methoxybenzyl)-5-methyl-imidazo[1,5- a ]imidazole-2-one. The synthetic potential of this scaffold was demonstrated by displacing bromine by Suzuki-Miyaura cross-coupling reactions. A large panel of boronic acids (aryl, heteroaryl or vinyl) were easily introduced, giving access to a broad and diversified library of 1-(4-methoxybenzyl)-5-methyl-7-(substituted)-imidazo[1,5- a ]imidazole-2-ones. A pathway to new 7-bromo-1-(4-methoxybenzyl)-5-methyl-imidazo[1,5- a ]imidazole-2-one was reported. The synthetic potential of this scaffold was demonstrated by displacing bromine by Suzuki-Miyaura cross-coupling reactions.