Hydrogen-bond-induced Aza-Michael addition of imidazoles and quinones without additional base and DFT calculations

Abstract

We reported a hydrogen-bond-induced aza-Michael addition of imidazoles to quinones. For the reactions, a simple one-pot operation was conducted without any additives. A range of imidazoles reacted with quinones to yield the corresponding products in moderate to excellent yields (31 examples, up to 92 % yield). Some drug and natural N-heterocyclic molecules were also compatible under these conditions. Notably, all reactant atoms were converted into the unique products, and dimethyl carbonate (DMC) was recyclable. Furthermore, density functional theory (DFT) calculations confirmed the hydrogen-bond-induced process and elucidated the mechanism.