Efficient Synthesis of 3‐Phenylnaphtho[2,3‐b]furan‐4,9‐diones in Water and Their Fluorimetric Study in Solutions |
| |
Authors: | Renzun Zhang Dongcheng Xu Jianwu Xie |
| |
Affiliation: | Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Department of Chemistry and Life Sciences, Zhejiang Normal University, Jinhua, Zhejiang 321004, China |
| |
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). |
| |
Keywords: | domino reaction naphthoquinones fluorescence Michael addition 2‐hydroxynaphthalene‐1,4‐dione |
|
|