Navegar

Colección

Datos Estadísticas

Artículo

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" (2004) Tetrahedron Letters. 45(48):8935-8939
La versión final de este artículo es de uso interno. El editor solo permite incluir en el repositorio el artículo en su versión post-print. Por favor, si usted la posee enviela a
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor

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
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
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
Volumen:45
Número:48
Página de inicio:8935
Página de fin:8939
DOI: http://dx.doi.org/10.1016/j.tetlet.2004.09.183
Título revista:Tetrahedron Letters
Título revista abreviado:Tetrahedron Lett.
ISSN:00404039
CODEN:TELEA
CAS:toluene, 108-88-3
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404039_v45_n48_p8935_Romanelli

Referencias:

  • O'Kennedy, R., Zhorenes, R., (1997) Coumarins: Biology, Applications and Mode of Action, , John Wiley and Sons Chichester
  • Takadate, A., Tahara, T., Fujino, H., Goya, S., (1982) Chem. Pharm. Bull., 30, pp. 4120-4125
  • Jiménez, M., Mateo, J.J., Mateo, R., (2000) J. Chromatogr. a, 870, pp. 473-481
  • Mitra, A.K., De, A., Karchaudhuri, N., Misra, S.K., Mukopadhyay, A.K., (1998) J. Indian Chem. Soc., 75, pp. 666-671
  • Cravotto, G., Nano, G.M., Palmisano, G., Tagliapietra, S., (2001) Tetrahedron: Asymmetry, 12, pp. 707-709
  • Kayser, O., Kolodziej, H., (1997) Planta Med., 63, pp. 508-510
  • Wang, C.J., Hsieh, Y.J., Chu, C.Y., Lin, Y.L., Tseng, T.H., (2002) Cancer Lett., 183, pp. 163-168
  • Fan, G.-J., Mar, W., Park, M.K., Wook Choi, E., Kim, K., Kim, S., (2001) Bioorg. Med. Chem. Lett., 11, pp. 2361-2363
  • Kirkiacharian, S., Thuy, D.T., Sicsic, S., Bakhchinian, R., Kurkjian, R., Tonnaire, T., (2002) Il Farmaco, 57, pp. 703-708
  • Sethna, S., Phadke, R., (1953) Org. React., 7, pp. 1-58
  • Furniss, B.S., Hannaford, A.J., Rogers, V., Smith, P.W.G., Tatchell, A.R., (1978) Vogel's Textbook of Practical Organic Chemistry, , Longman New York
  • Laufer, M.C., Hausmann, H., Hoelderich, W.F., (2003) J. Catal., 218, pp. 315-320
  • Biswas, G.K., Basu, K., Barua, A.K., Bhattacharya, P., (1992) Indian J. Chem. Sect. B, 31, pp. 628-630
  • Li, T.-S., Zhang, Z.-H., Yang, F., Fu, Ch.-G., (1998) J. Chem. Res. (S), pp. 38-39
  • Subba Rao, Y.B., Kulkarni, S.J., Subrahmanyam, M., Rama Rao, A.V., (1993) J. Chem. Soc., Chem. Commun., pp. 1456-1457
  • Hoefnagel, A.J., Gunnewegh, E.A., Downing, R.S., Van Bekkum, H., (1995) J. Chem. Soc., Chem. Commun., pp. 225-226
  • De La Hoz, A., Moreno, A., Vázquez, E., (1999) Synlett, pp. 608-610
  • Subhas Bose, D., Rudradas, A.P., Hari Babu, M., (2002) Tetrahedron Lett., 43, pp. 9195-9197
  • Reddy, B.M., Reddy, V.R., Giridhar, D., (2001) Synth. Commun., 31, pp. 3603-3607
  • Palaniappan, S., Sekhar, R.C., (2004) J. Mol. Catal. a, 209, pp. 117-124
  • Ramani, A., Chanda, B.M., Velu, S., Sivasanker, S., (1999) Green Chem., 1, pp. 163-165
  • Potdar, M.K., Mohile, S.S., Salunkhe, M.M., (2001) Tetrahedron Lett., 42, pp. 9285-9287
  • Frère, S., Thiéry, V., Besson, T., (2001) Tetrahedron Lett., 42, pp. 2791-2794
  • Kozhevnikov, I., (1998) Chem. Rev., 98, pp. 171-198
  • Romanelli, G.P., Baronetti, G., Thomas, H.J., Autino, J.C., (2003) Tetrahedron Lett., 44, pp. 1301-1303
  • Romanelli, G.P., Autino, J.C., Baronetti, G., Thomas, H.J., unpublished results; Baronetti, G., Briand, L., Sedran, U., Thomas, H., (1998) Appl. Catal. a, 172, pp. 265-272

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