Zirconium-catalyzed one-pot synthesis of benzoxazoles using reaction of catechols, aldehydes and ammonium acetate

Abstract

Abstract In this study, an efficient method for the synthesis of benzoxazoles by coupling catechols, aldehydes and ammonium acetate using ZrCl4 as catalyst in ethanol is reported. A wide range of benzoxazoles (59 examples) are smoothly produced in high yields (up to 97%). Other advantages of the method include large-scale synthesis and the use of oxygen as an oxidant. The mild reaction conditions allowed late-stage functionalization, facilitating access to several derivatives with biologically relevant structures such as β-lactam and quinoline heterocycles.