Multicomponent cascade reaction of 3-formylchromones: Highly regioselective synthesis of functionalized pyridin-2(1H)-ones

Abstract

A novel protocol was developed for the construction of highly functionalized pyridin-2(1H)-ones from 3-formylchromones, ethyl 2-(pyridin-2-yl)acetate derivatives and amines via a complex multicomponent cascade reaction involving targeted duplicated ring-opening and duplicated cyclization reactions which form skeleton-reorganized target compounds. A series of pyridin-2(1H)-ones were produced by this reaction accompanied by the formation of three bonds (one C–N and two C–C bonds) and the cleavage of one bond in one step. This protocol can be used in combinatorial and parallel syntheses of various pyridin-2(1H)-ones with potent biological activity. The advantages of this approach include simple and practical operation (multicomponent one-pot), high yields (up to 91%), and products with potential biological activity.

Keywords

• Pyridin-2(1H)-ones
• Cascade reaction
• Selective synthesis
• 3-Formylchromones