Discovery of intermolecular cascade annulation for dihydrobenzo[b][1,8]naphthyridine-ylidene-pyrrolidinetriones†

Abstract

Developing efficient procedures for the synthesis of combinations of pharmacophores continues to be a vital objective in synthetic science. Herein, we report an unprecedented family of dihydrobenzo[b][1,8]naphthyridine-ylidene-pyrrolidinetriones achieved by reacting ortho-halogenated quinolonechalcones with aminomaleimides under metal-free conditions. Among these compounds, several exhibit the potential to serve as fluorescent dyes for biological applications. Mechanistic investigations indicate that the reaction proceeds via a 1,4-Michael addition followed by an intermolecular cascade annulation, which involves aniline fragment transfer and S_NAr processes. As far as we know, studies regarding the synthesis of dihydrobenzo[b][1,8]naphthyridine-ylidene-pyrrolidinetriones are rare. This discovery offers great inspiration for a feasible approach toward the creation of more complex and useful molecules.