Visible-Light 2,4-Dinitrophenol-Mediated Photoannulation of α-Azidochalcones into 2,5-Diaryloxazoles.

A novel and efficient visible-light 2,4-dinitrophenol (2,4-DNP) mediated photoannulation of α-azidochalcones into 2,5-diaryloxazoles was developed. The carbon-carbon double bond of α-azidochalcone was cleaved, leading to the formation of new C-O and C-N bonds in the photoannulation. Control experiments were carried out, and a plausible mechanism of the photoannulation was proposed. The scope of the reaction was studied by synthesizing a series of 2,5-diaryloxazoles including two naturally occurring oxazoles (Texamine and Balsoxin) in excellent yields.