A procedure was developed for the synthesis of fluorinated 2-aminopyridines based on the reactions of 1,1-enediamines, benzaldehydes and 1,3-dicarbonyl compounds.

A concise and eco-friendly route for the synthesis of highly functionalized bicyclic pyridinium derivatives (3) via a one-pot reaction of chromone-3-carboxaldehydes (1) and N-benzyl nitro ketene aminals (NBNKAs) (2) under reflux in ethanol media has been developed. The targeted compound was efficiently obtained by filtration without further post-treatment. In the one-pot two step reaction, CC and CN bonds were constructed, while at the same time one CO bond was cleaved. This protocol represents a valuable route to obtain highly functional bicyclic pyridinium derivatives in a concise, rapid, and practical manner. The reaction is particularly attractive due to features such as low cost, mild conditions, atom economy, high yield, using biocompatible solvent, and potential biological activity of the product.

The methods for selective synthesis of two novel types of compounds including pyridin-2-ones 3 and pyrimidin-4-ones 4 were developed. The antitumor bioactivity screening showed that certain compounds had potent antitumor activity.