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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| Published in | Chinese journal of chemistry Vol. 30; no. 8; pp. 1690 - 1694 |
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| Main Author | |
| Format | Journal Article |
| Language | English |
| Published |
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WILEY-VCH Verlag
01.08.2012
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| 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 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）. |
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| AbstractList | 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 conditions [NaOAc (120 mol%), water, 70 degrees 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 (432433 nm), green light (512536 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 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). 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). 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 and 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 [alpha]-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). 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）. |
| Author | Xu, Dongcheng Xie, Jianwu Zhang, Renzun |
| AuthorAffiliation | Key Laboratory of the Ministry of Education for Advanced Catalysis＇ Materials, Department of Chemistry and Life Sciences, Zhejiang Normal University, Jinhua, Zhejiang 321004, China |
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| CitedBy_id | crossref_primary_10_1002_slct_201800396 crossref_primary_10_1016_j_bmc_2020_115565 crossref_primary_10_1016_j_ejmech_2018_03_079 crossref_primary_10_1016_j_tetlet_2017_08_027 crossref_primary_10_1002_ejoc_201300996 crossref_primary_10_1039_C5RA19619A crossref_primary_10_1016_j_ejmech_2019_06_056 crossref_primary_10_1039_D4OB00221K crossref_primary_10_1039_C6AY01786J crossref_primary_10_1039_D4RA02474E crossref_primary_10_1039_D4RA08843C |
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| Keywords | 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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| Notes | 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 |
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| Snippet | 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... 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... 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... 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 [alpha]-bromonitroalkenes... |
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| SubjectTerms | 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 |
| Title | Efficient Synthesis of 3-Phenylnaphtho[2,3-b]furan-4,9-diones in Water and Their Fluorimetric Study in Solutions |
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