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Keywords:

  • domino reaction;
  • naphthoquinones;
  • fluorescence;
  • Michael addition;
  • 2-hydroxynaphthalene-1,4-dione

Abstract

A simple and efficient protocol has been developed for the synthesis of 3-phenylnaphtho[2,3-b]furan-4,9-diones by domino reaction of α-bromonitroalkenes to 2-hydroxynaphthalene-1,4-dione. With the optimal reaction conditions [NaOAc (120 mol%), water, 70°C, 7 h], the scope of the domino reaction was explored and the green approach provided the desired products in moderate to good yields at elevated temperature under aqueous-mediated conditions. A mechanistic rationalization for this reaction is also provided. The absorption characteristics of the compounds were examined by UV-Vis spectra and fluorescence spectroscopy. All compounds were fluorescent in solution emitting at blue light (432–433 nm), green light (512–536 nm), or yellow light (591 nm).