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

Abstract

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.

Graphical Abstract

Keywords:

• Phenyliodine(III) diacetate
• 2-(2-hydroxynaphthyl)benzoxazoles
• 1-(benzoxazol-2-yl)-1-alkoxynaphthalen-2(1H)-ones
• 1-(benzoxazol-2-yl)naphthalene-2,3-dione

Acknowledgments

All the spectra were obtained at Dr. APJ Abdul Kalam Central Instrumentation Laboratory, GJUST, Hisar, and SCXRD were recorded at Panjab University, Chandigarh.

Disclosure statement

No potential conflict of interest was reported by the author(s).

Additional information

Funding

Geeta Yadav is thankful to the Council of Scientific and Industrial Research (CSIR), New Delhi for financial support. Dr. Ramesh Kataria thanks DST FIST II for financial support to Panjab University for the single crystal facility.