Phenyliodine(III) diacetate-induced regioselective synthesis of 1-(benzoxazol-2-yl)-1-alkoxynaphthalen-2(1H)-ones from 2-(2-hydroxynaphthyl)benzoxazoles

Phenyliodine(III) diacetate-induced oxidation of 2-(2-hydroxynaphthyl)benzoxazoles in alcohols, regioselectively afforded dearomatized products: 1-(benzoxazol-2-yl)-1-alkoxynaphthalen-2(1H)-ones and 1-(benzoxazol-2-yl)naphthalene-2,3-diones. Further, these products were also synthesized in one-pot either from (E)-1-(((2-hydroxyphenyl) imino)methyl)naphthalen-2-ol or 2-aminophenol and 2-hydroxynaphthaldehyde by varying the amount of phenyliodine(III) diacetate in different alcohols. The structure of these compounds was established on the basis of FTIR, NMR, and mass spectral data as well as X-ray crystallographic data.