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

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 w...

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Bibliographic Details
Published inChinese journal of chemistry Vol. 30; no. 8; pp. 1690 - 1694
Main Author 张仁尊 徐东成 谢建武
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 01.08.2012
WILEY‐VCH Verlag
Wiley
Wiley Subscription Services, Inc
Subjects
2-hydroxynaphthalene-1
2‐hydroxynaphthalene‐1,4‐dione
4-dione
Chemistry
Chemistry, Multidisciplinary
domino reaction
fluorescence
High temperature
Michael addition
NaOAc
naphthoquinones
Physical Sciences
Science & Technology
UV-Vis光谱
二酮
合成
呋喃
最佳反应条件
水
荧光光谱
Michael addition
CANCER CELLS
ONE-POT
NUCLEOPHILIC-SUBSTITUTION
4-dione
ANTIBACTERIAL
BETA-LAPACHONE
fluorescence
naphthoquinones
ANTIFUNGAL
domino reaction
DERIVATIVES
1,4-QUINONES
NITROALKENES
2-hydroxynaphthalene-1
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Summary: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）.
Bibliography:31-1547/O6
Zhan, Renzun, Xu Dongcheng, Xie Jianwu（ Key Laboratory of the Ministry of Education for Advanced Catalysis＇ Materials, Department of Chemistry and Life Sciences, Zhejiang Normal University, Jinhua, Zhejiang 321004, China）
domino reaction, naphthoquinones, fluorescence, Michael addition, 2-hydroxynaphthalene-1,4-dione
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）.
istex:A67AE285F66EC4329288BF6AA53CA87DC2045257
the National Natural Science Foundation of China - No. 20902083
ark:/67375/WNG-0CDFW89X-N
ArticleID:CJOC201200499
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 14
ISSN:1001-604X
1614-7065
DOI:10.1002/cjoc.201200499