Aerobic primary and secondary amine oxidation cascade by a copper amine oxidase inspired catalyst

Abstract

Herein, we report a bioinspired catalytic system for the one-pot cascade oxidation of a native primary amine and an in situ generated non-native secondary amine. The catalyst consists of an o-quinone cofactor phd (1,10-phenanthroline-5,6-dione) and a copper ion and operates under ambient air conditions. Quinazolin-4(3H)-ones, which are common pharmacophores present in numerous pharmaceuticals and bioactive compounds, were synthesized in high yields. A detailed kinetic and mechanistic study elucidates the role of the catalyst in the multi-step oxidative cascade reaction.