A solvent-free synthesis of coumarins using a Wells-Dawson heteropolyacid as catalyst
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....
Guardado en:
| Autor principal: | |
|---|---|
| Otros Autores: | , , , , |
| Formato: | Capítulo de libro |
| Lenguaje: | Inglés |
| Publicado: |
2004
|
| Acceso en línea: | Registro en Scopus DOI Handle Registro en la Biblioteca Digital |
| Aporte de: | Registro referencial: Solicitar el recurso aquí |
| LEADER | 06947caa a22009737a 4500 | ||
|---|---|---|---|
| 001 | PAPER-4359 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518203354.0 | ||
| 008 | 190411s2004 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-7444233600 | |
| 024 | 7 | |2 cas |a toluene, 108-88-3 | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a TELEA | ||
| 100 | 1 | |a Romanelli, G.P. | |
| 245 | 1 | 2 | |a A solvent-free synthesis of coumarins using a Wells-Dawson heteropolyacid as catalyst |
| 260 | |c 2004 | ||
| 270 | 1 | 0 | |m Lab. Estud. de Compuestos Organicos, Facultad de Ciencias Exactas, Univ. Nac. Plata, Calles 47 Y.Argentina; email: jautino@quimica.unlp.edu.ar |
| 506 | |2 openaire |e Política editorial | ||
| 504 | |a O'Kennedy, R., Zhorenes, R., (1997) Coumarins: Biology, Applications and Mode of Action, , John Wiley and Sons Chichester | ||
| 504 | |a Takadate, A., Tahara, T., Fujino, H., Goya, S., (1982) Chem. Pharm. Bull., 30, pp. 4120-4125 | ||
| 504 | |a Jiménez, M., Mateo, J.J., Mateo, R., (2000) J. Chromatogr. a, 870, pp. 473-481 | ||
| 504 | |a Mitra, A.K., De, A., Karchaudhuri, N., Misra, S.K., Mukopadhyay, A.K., (1998) J. Indian Chem. Soc., 75, pp. 666-671 | ||
| 504 | |a Cravotto, G., Nano, G.M., Palmisano, G., Tagliapietra, S., (2001) Tetrahedron: Asymmetry, 12, pp. 707-709 | ||
| 504 | |a Kayser, O., Kolodziej, H., (1997) Planta Med., 63, pp. 508-510 | ||
| 504 | |a Wang, C.J., Hsieh, Y.J., Chu, C.Y., Lin, Y.L., Tseng, T.H., (2002) Cancer Lett., 183, pp. 163-168 | ||
| 504 | |a Fan, G.-J., Mar, W., Park, M.K., Wook Choi, E., Kim, K., Kim, S., (2001) Bioorg. Med. Chem. Lett., 11, pp. 2361-2363 | ||
| 504 | |a Kirkiacharian, S., Thuy, D.T., Sicsic, S., Bakhchinian, R., Kurkjian, R., Tonnaire, T., (2002) Il Farmaco, 57, pp. 703-708 | ||
| 504 | |a Sethna, S., Phadke, R., (1953) Org. React., 7, pp. 1-58 | ||
| 504 | |a 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 | ||
| 504 | |a Laufer, M.C., Hausmann, H., Hoelderich, W.F., (2003) J. Catal., 218, pp. 315-320 | ||
| 504 | |a Biswas, G.K., Basu, K., Barua, A.K., Bhattacharya, P., (1992) Indian J. Chem. Sect. B, 31, pp. 628-630 | ||
| 504 | |a Li, T.-S., Zhang, Z.-H., Yang, F., Fu, Ch.-G., (1998) J. Chem. Res. (S), pp. 38-39 | ||
| 504 | |a Subba Rao, Y.B., Kulkarni, S.J., Subrahmanyam, M., Rama Rao, A.V., (1993) J. Chem. Soc., Chem. Commun., pp. 1456-1457 | ||
| 504 | |a Hoefnagel, A.J., Gunnewegh, E.A., Downing, R.S., Van Bekkum, H., (1995) J. Chem. Soc., Chem. Commun., pp. 225-226 | ||
| 504 | |a De La Hoz, A., Moreno, A., Vázquez, E., (1999) Synlett, pp. 608-610 | ||
| 504 | |a Subhas Bose, D., Rudradas, A.P., Hari Babu, M., (2002) Tetrahedron Lett., 43, pp. 9195-9197 | ||
| 504 | |a Reddy, B.M., Reddy, V.R., Giridhar, D., (2001) Synth. Commun., 31, pp. 3603-3607 | ||
| 504 | |a Palaniappan, S., Sekhar, R.C., (2004) J. Mol. Catal. a, 209, pp. 117-124 | ||
| 504 | |a Ramani, A., Chanda, B.M., Velu, S., Sivasanker, S., (1999) Green Chem., 1, pp. 163-165 | ||
| 504 | |a Potdar, M.K., Mohile, S.S., Salunkhe, M.M., (2001) Tetrahedron Lett., 42, pp. 9285-9287 | ||
| 504 | |a Frère, S., Thiéry, V., Besson, T., (2001) Tetrahedron Lett., 42, pp. 2791-2794 | ||
| 504 | |a Kozhevnikov, I., (1998) Chem. Rev., 98, pp. 171-198 | ||
| 504 | |a Romanelli, G.P., Baronetti, G., Thomas, H.J., Autino, J.C., (2003) Tetrahedron Lett., 44, pp. 1301-1303 | ||
| 504 | |a 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 | ||
| 520 | 3 | |a 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. |l eng | |
| 536 | |a Detalles de la financiación: Comisión de Investigaciones Científicas | ||
| 536 | |a Detalles de la financiación: Fundación Antorchas | ||
| 536 | |a Detalles de la financiación: Universidad Nacional de La Plata, UNLP | ||
| 536 | |a Detalles de la financiación: We thank to Fundación Antorchas, to Universidad Nacional de La Plata and to Comisión de Investigaciones Científicas de la Provincia de Buenos Aires for financial support. H.J.T., G.P.R. and G.B. are members of CONICET. | ||
| 593 | |a Lab. Estud. de Compuestos Organicos, Facultad de Ciencias Exactas, Univ. Nac. Plata, Calles 47 Y., Argentina | ||
| 593 | |a Ctro. Invest. Y Desarrollo Cie. A., Facultad de Ciencias Exactas, Univ. Nac. Plata-CONICET, C., Argentina | ||
| 593 | |a Curso de Quím. Orgán., Fac. de Cie. Agrarias Y Forestales, Univ. Nac. Plata, Calles 60 Y., Argentina | ||
| 593 | |a Depto. de Ingeniera Quim., Fac. de Ciencias Exactas Y Naturales, Univ. Buenos Aires, Cd. Univ., C., Argentina | ||
| 690 | 1 | 0 | |a 4-METHYLUMBELLIFERONE |
| 690 | 1 | 0 | |a COUMARIN |
| 690 | 1 | 0 | |a HETEROPOLYACID |
| 690 | 1 | 0 | |a PECHMANN REACTION |
| 690 | 1 | 0 | |a WELLS-DAWSON CATALYST |
| 690 | 1 | 0 | |a COUMARIN DERIVATIVE |
| 690 | 1 | 0 | |a SOLVENT |
| 690 | 1 | 0 | |a TOLUENE |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a CATALYST |
| 690 | 1 | 0 | |a DRUG SYNTHESIS |
| 690 | 1 | 0 | |a HIGH TEMPERATURE |
| 690 | 1 | 0 | |a POLYMERIZATION |
| 690 | 1 | 0 | |a QUANTUM YIELD |
| 690 | 1 | 0 | |a REACTION ANALYSIS |
| 690 | 1 | 0 | |a SUBSTITUTION REACTION |
| 690 | 1 | 0 | |a TEMPERATURE DEPENDENCE |
| 700 | 1 | |a Bennardi, D. | |
| 700 | 1 | |a Ruiz, D.M. | |
| 700 | 1 | |a Baronetti, G. | |
| 700 | 1 | |a Thomas, H.J. | |
| 700 | 1 | |a Autino, J.C. | |
| 773 | 0 | |d 2004 |g v. 45 |h pp. 8935-8939 |k n. 48 |p Tetrahedron Lett. |x 00404039 |w (AR-BaUEN)CENRE-415 |t Tetrahedron Letters | |
| 856 | 4 | 1 | |u https://www.scopus.com/inward/record.uri?eid=2-s2.0-7444233600&doi=10.1016%2fj.tetlet.2004.09.183&partnerID=40&md5=933aac0737debb5bd25a06c17fe3e3b1 |y Registro en Scopus |
| 856 | 4 | 0 | |u https://doi.org/10.1016/j.tetlet.2004.09.183 |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_00404039_v45_n48_p8935_Romanelli |y Handle |
| 856 | 4 | 0 | |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404039_v45_n48_p8935_Romanelli |y Registro en la Biblioteca Digital |
| 961 | |a paper_00404039_v45_n48_p8935_Romanelli |b paper |c PE | ||
| 962 | |a info:eu-repo/semantics/article |a info:ar-repo/semantics/artículo |b info:eu-repo/semantics/publishedVersion | ||
| 963 | |a VARI | ||
| 999 | |c 65312 | ||