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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
Institution: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‐phenylnaphtho2,3‐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
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