Synthesis of dihydropyrimidone-4-one derivatives from amines, phenyl cyanides and acetylenedicarboxylate

The pyrimidone skeletons exist in the core structure of several biologically active compounds, such as calcium receptor (CaR) antagonist, methaqualone, GnRH receptor antagonist and angiotensin II (A II) receptor antagonist. Evodiamine, amajor quinazolinocarbolin alkaloid isolated from the fruit of Evodia rutaecarpa Bentham, has been reported exhibiting vasorelaxant and cardiotonic effects [1,2]. Although several methods for synthesis of pyrimidone fused pyrimidones derivatives have been developed [3]. Most of these protocols suffer from tedious procedures, poor precursor scopes, and/or low efficiency. Therefore the development of the facile methodologies for the generation of highly functionalized pyrimidone derivatives library is still challenging in organic synthetic chemistry and medicinal chemistry. Here we wish to report the result of our study on the reaction of amines 1, phenyl cyanides 2 and acetylenedicarboxylate 3 lead to dihydropyrimidone-4-one derivatives 4. The structures of this products were proved by 1H-NMR, 13C-NMR and IR spectral data.