Synthesis of polyfunctional fluoro-quinoline and fluoro-pyridopyrimidinone derivatives

2-Fluoromalonic acid is a useful building block for the synthesis of selectively fluorinated heterocycles. In the presence of phosphoryl chloride, chlorinated fluoro-quinoline and fluoro-pyridopyrimidinone derivatives can be prepared in a single step by an efficient tandem chlorination-cyclisation process. Functionalisation by Suzuki cross-coupling or SNAr processes allowed for the rapid construction of a small library of 30 novel polysubstituted selectively fluorinated quinoline and pyridopyrimidinone derivatives in high yields and bearing a diverse range of substituents.