Abstract:
Seventeen examples are resolved, most of them in good to excellent yields, using the cheap WD catalyst. Substituted coumarins are synthesized from phenols and β-ketoesters by the Pechmann reaction, using a Wells-Dawson heteropolyacid (H 6P 2W 18O 62• 24H 2O) as catalyst by a solvent-free procedure. This one requires low reaction times, 130°C temperature and as little as 1 mol % of Wells-Dawson acid, obtaining good to excellent yields of coumarins. The catalyst showed to be reusable with no differences in the yields. The results are compared with those of the reactions performed in toluene solution. The presented synthetic procedure is a convenient, clean and fast alternative for synthesizing 4-substituted coumarins (17 examples). © 2004 Elsevier Ltd. All rights reserved.
Registro:
Documento: |
Artículo
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Título: | A solvent-free synthesis of coumarins using a Wells-Dawson heteropolyacid as catalyst |
Autor: | Romanelli, G.P.; Bennardi, D.; Ruiz, D.M.; Baronetti, G.; Thomas, H.J.; Autino, J.C. |
Filiación: | Lab. Estud. de Compuestos Organicos, Facultad de Ciencias Exactas, Univ. Nac. Plata, Calles 47 Y., Argentina Ctro. Invest. Y Desarrollo Cie. A., Facultad de Ciencias Exactas, Univ. Nac. Plata-CONICET, C., Argentina Curso de Quím. Orgán., Fac. de Cie. Agrarias Y Forestales, Univ. Nac. Plata, Calles 60 Y., Argentina Depto. de Ingeniera Quim., Fac. de Ciencias Exactas Y Naturales, Univ. Buenos Aires, Cd. Univ., C., Argentina
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Palabras clave: | 4-Methylumbelliferone; Coumarin; Heteropolyacid; Pechmann reaction; Wells-Dawson catalyst; coumarin derivative; solvent; toluene; article; catalyst; drug synthesis; high temperature; polymerization; quantum yield; reaction analysis; substitution reaction; temperature dependence |
Año: | 2004
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Volumen: | 45
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Número: | 48
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Página de inicio: | 8935
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Página de fin: | 8939
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DOI: |
http://dx.doi.org/10.1016/j.tetlet.2004.09.183 |
Título revista: | Tetrahedron Letters
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Título revista abreviado: | Tetrahedron Lett.
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ISSN: | 00404039
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CODEN: | TELEA
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CAS: | toluene, 108-88-3
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404039_v45_n48_p8935_Romanelli |
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Citas:
---------- APA ----------
Romanelli, G.P., Bennardi, D., Ruiz, D.M., Baronetti, G., Thomas, H.J. & Autino, J.C.
(2004)
. A solvent-free synthesis of coumarins using a Wells-Dawson heteropolyacid as catalyst. Tetrahedron Letters, 45(48), 8935-8939.
http://dx.doi.org/10.1016/j.tetlet.2004.09.183---------- CHICAGO ----------
Romanelli, G.P., Bennardi, D., Ruiz, D.M., Baronetti, G., Thomas, H.J., Autino, J.C.
"A solvent-free synthesis of coumarins using a Wells-Dawson heteropolyacid as catalyst"
. Tetrahedron Letters 45, no. 48
(2004) : 8935-8939.
http://dx.doi.org/10.1016/j.tetlet.2004.09.183---------- MLA ----------
Romanelli, G.P., Bennardi, D., Ruiz, D.M., Baronetti, G., Thomas, H.J., Autino, J.C.
"A solvent-free synthesis of coumarins using a Wells-Dawson heteropolyacid as catalyst"
. Tetrahedron Letters, vol. 45, no. 48, 2004, pp. 8935-8939.
http://dx.doi.org/10.1016/j.tetlet.2004.09.183---------- VANCOUVER ----------
Romanelli, G.P., Bennardi, D., Ruiz, D.M., Baronetti, G., Thomas, H.J., Autino, J.C. A solvent-free synthesis of coumarins using a Wells-Dawson heteropolyacid as catalyst. Tetrahedron Lett. 2004;45(48):8935-8939.
http://dx.doi.org/10.1016/j.tetlet.2004.09.183