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Abstract:

A facile photochemical preparation of 5-, 6-, and 7-substituted chroman-4-ones from aryl 3-methyl-2-butenoate esters is described. The two-phase base-catalyzed method relies upon two consecutive processes in one-pot reaction through a photo-Fries rearrangement and a based-catalyzed intramolecular oxa-Michael addition to afford the desired products. © 2014 Elsevier Ltd.

Registro:

Documento: Artículo
Título:Expeditious photochemical reaction toward the preparation of substituted chroman-4-ones
Autor:Iguchi, D.; Erra-Balsells, R.; Bonesi, S.M.
Filiación:CIHIDECAR - CONICET, Departamento de Química Orgánica, University of Buenos Aires, Buenos Aires, 1428, Argentina
Palabras clave:Aryl esters; Chroman-4-ones; oxa-Michael addition; photo-Fries rearrangement; Two-phase reaction; 3 methyl 2 butenoate ester derivative; 4 chromanone derivative; cyclohexane; ester derivative; natural product; unclassified drug; Article; catalysis; cyclization; Michael addition; photochemistry; quantum yield; reaction analysis
Año:2014
Volumen:55
Número:33
Página de inicio:4653
Página de fin:4656
DOI: http://dx.doi.org/10.1016/j.tetlet.2014.06.081
Título revista:Tetrahedron Letters
Título revista abreviado:Tetrahedron Lett.
ISSN:00404039
CODEN:TELEA
CAS:cyclohexane, 110-82-7
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404039_v55_n33_p4653_Iguchi

Referencias:

  • Dean, F.M., (1963) Naturally Occuring Oxygen Ring Compounds, , Butherworths London
  • Ellis, G.P., Lockhart, I.M., (1977) Chromans and Tocopherols, , Wiley New York
  • Green, G., Evans, J.M., Vong, A.K., (1996) Comprehensive Heterocyclic Chemistry II, 5, p. 469. , A. Mc Killop, Pergamon Oxford
  • Hodgetts, K.J., Maragkou, K.I., Wallace, T.W., Wootton, C.R., (2001) Tetrahedron, 57, pp. 6793-6804
  • Fridin Saxim, M., Pemberton, N., Andersson, K., Da, S., Dayrager, C., Friberg, A., Grotli, M., Luthman, K., (2009) J. Org. Chem., 74, pp. 2755-2759
  • Takikawa, H., Suzuki, K., (2007) Org. Lett., 9, pp. 2713-2716
  • Lipinski, C.A., Aldinger, C.E., Beyer, T.A., Bordner, J., Bussolotti, D.F., Inskeep, P.B., Siegel, T.W., (1992) J. Med. Chem., 35, pp. 2169-2177
  • Butler, J.D., Conrad, W.E., Lodewyk, M.W., Fettinger, J.C., Tantillo, D.J., Kurth, M.J., (2010) Org. Lett., 12, pp. 3410-3413
  • Pritchard, R.G., Sheldrake, H.M., Taylor, I.Z., Wallace, T.W., (2008) Tetrahedron Lett., 49, pp. 4156-4159
  • Irsay, R.D., (1972), U.S. Patent N 3678170; Macdonald, J.E., Hysell, M.K., Lui, Q., Yu, D., Ke, N., Liu, G., Li, H.Q.X., Wong-Staal, F., (2008), WO N° 067451; Meng, L.-G., Liu, H.-F., Wei, J.-L., Gong, S.-N., Xue, S., (2010) Tetrahedron Lett., 51, pp. 1748-1750
  • Roy, O., Loiseau, F., Riahi, A., Henin, F., Muzart, J., (2003) Tetrahedron, 59, p. 9641. , Friedel-Craft reaction
  • Draper, R.W., Hu, B., Iyer, R.V., Li, X., Lu, Y., Rahman, M., Vater, E.J., (2000) Tetrahedron, 56, p. 1811
  • Derrick, I.A.R., Igbal, M., Livingstone, R., McGreeny, B.J., (1999) J. Chem. Res. (S), p. 530
  • Sebok, P., Jeko, J., Timar, T., Jaszberenyi, J.C., (1994) Heterocycles, 38, p. 2099
  • Amaral, A.C.F., Barnes, R.A., (1992) J. Heterocycl. Chem., 29, p. 1457
  • Teixidor, P., Camps, F., Messeguer, A., (1988) Heterocycles, 27, p. 2459
  • Timar, T., Jaszberenyi, J.C., (1988) J. Heterocycl. Chem., 25, p. 871
  • Timar, T., Hoszrafi, S., Jaszberenyi, J.C., Kover, K.E., Batta, G., (1988) Acta Chim. Hung., 125, p. 303
  • Piccolo, O., Fillippini, L., Tinucci, L., Valoti, E., Cittero, A., (1986) Tetrahedron, 42, p. 885
  • Tsukayama, M., (1975) Bull. Chem. Soc. Jpn., 48, p. 80
  • Anjaneyulu, A.S.R., Isaa, B., (1991) J. Chem. Soc., Perkin Trans. 1, p. 2089. , Claisen rearrangement reaction
  • Ariamala, G., Balasubramarnan, K.K., (1989) Tetrahedron, 45, p. 309
  • Rohatgi, B.K., Grupta, R.S., Khanna, R.N., (1981) Indian J. Chem., Sect B, 20, p. 505
  • Hlubucek, J., Ritchie, E., Taylor, W.C., (1969) Tetrahedron Lett., 17, p. 1369
  • Kabbe, H.J., Widdig, A., (1982) Angew. Chem., Int. Ed., 21, p. 247. , Kabbe condensation reaction
  • Paradkar, M.V., Godbole, H.M., Ranade, A.A., Joseph, A.R., (1998) J. Chem. Res. (S), p. 318
  • Miranda, M.A., Primo, J., Tormo, R., (1987) Tetrahedron, 43, p. 2323
  • Garcia, H., Iborra, S., Primo, J., Miranda, M.A., (1986) J. Org. Chem., 51, p. 4432
  • Primo, J., Tormo, R., Miranda, M.A., (1982) Heterocycles, 19, p. 1819
  • Samaniego López, C., Erra-Balsells, R., Bonesi, S.M., (2010) Tetrahedron Lett., 51, pp. 4387-4390
  • Perlmutter, P., (1992) Conjugate Addition Reactions in Organic Synthesis, p. 126. , Pergamon Oxford
  • Baldwin, J.E., Thomas, R.C., Kruse, L.I., Silberman, L., (1977) J. Org. Chem., 42, p. 3846
  • Braslavsky, S.E., Kuhn, H.J., (1987) Provisional List of Actinometers Comission III.3, Photochemistry, , IUPAC Mulhein an der Ruhr
  • Parker, A.C., (1968) Photoluminiscence of Solutions with Applications to Photochemistry and Analytical Chemistry, , Elsevier Amsterdam, New York

Citas:

---------- APA ----------
Iguchi, D., Erra-Balsells, R. & Bonesi, S.M. (2014) . Expeditious photochemical reaction toward the preparation of substituted chroman-4-ones. Tetrahedron Letters, 55(33), 4653-4656.
http://dx.doi.org/10.1016/j.tetlet.2014.06.081
---------- CHICAGO ----------
Iguchi, D., Erra-Balsells, R., Bonesi, S.M. "Expeditious photochemical reaction toward the preparation of substituted chroman-4-ones" . Tetrahedron Letters 55, no. 33 (2014) : 4653-4656.
http://dx.doi.org/10.1016/j.tetlet.2014.06.081
---------- MLA ----------
Iguchi, D., Erra-Balsells, R., Bonesi, S.M. "Expeditious photochemical reaction toward the preparation of substituted chroman-4-ones" . Tetrahedron Letters, vol. 55, no. 33, 2014, pp. 4653-4656.
http://dx.doi.org/10.1016/j.tetlet.2014.06.081
---------- VANCOUVER ----------
Iguchi, D., Erra-Balsells, R., Bonesi, S.M. Expeditious photochemical reaction toward the preparation of substituted chroman-4-ones. Tetrahedron Lett. 2014;55(33):4653-4656.
http://dx.doi.org/10.1016/j.tetlet.2014.06.081