Microwave-assisted annulation for the construction of pyrido-fused heterocycles and their application as photoluminescent chemosensors

Abstract

A catalyst-free microwave-assisted annulation protocol for the preparation of biologically interesting pyrido-fused quinazolinones and pyrido[1,2-a]benzimidazoles is developed. This reaction involves the [3 + 3] annulation of various quinazolinones or benzimidazoles with 3-formylchromones to yield functionalized 11H-pyrido[2,1-b]quinazolin-11-one and pyrido[1,2-a] benzimidazole derivatives. This approach is successfully extended to the construction of various pyrazolo[4,3-d]pyrido[1,2-a]pyrimidin-10(1H)-ones. The present approach is complementary to the existing synthetic methodologies and offers a rapid and facile approach with a broad substrate scope, good yields, catalyst-free conditions, and a high functional group tolerance. The optimal synthesized compound is also employed as an “on–off” photoluminescent probe for the selective detection of Fe³⁺ and Ag⁺ metal ions.