Efficient Synthesis of 3-Phenylnaphtho[2,3-b]furan-4,9-diones in Water and Their Fluorimetric Study in Solutions  

作　　者：张仁尊 徐东成 谢建武 

机构地区：[1]Key Laboratory of the Ministry of Education for Advanced Catalysis'Materials,Department of Chemistry and Life Sciences,Zhejiang Normal University,Jinhua,Zhejiang 321004,China

出　　处：《Chinese Journal of Chemistry》2012年第8期1690-1694,共5页中国化学（英文版）

摘　　要：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 a-bromonitroalkenes to 2-hydroxynaphthalene-1,4-dione. With the optimal reaction condi- tions [NaOAc （120 mol%）, water, 70 ~C, 7 h], the scope of the domino reaction was explored and the green ap- proach 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）.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 a-bromonitroalkenes to 2-hydroxynaphthalene-1,4-dione. With the optimal reaction condi- tions [NaOAc （120 mol%）, water, 70 ~C, 7 h], the scope of the domino reaction was explored and the green ap- proach 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）.

关 键 词：domino reaction NAPHTHOQUINONES FLUORESCENCE Michael addition 2-hydroxynaphthalene-1 4-dione 

分 类 号：O614.33[理学—无机化学] O623.523[理学—化学]