Artículos de revistas
Expeditious Synthesis Of 3,4-dihydroisocoumarins And Phthalides Using The Heck-matsuda Reaction
Registro en:
Tetrahedron Letters. , v. 52, n. 48, p. 6342 - 6345, 2011.
404039
10.1016/j.tetlet.2011.09.014
2-s2.0-80255132030
Autor
Da Penha E.T.
Forni J.A.
Biajoli A.F.P.
Correia C.R.D.
Institución
Resumen
Several 3,4-dihydroisocoumarins and phthalides were synthesized by an effective Heck-Matsuda reaction involving an ortho carboxybenzenediazonium salt with a series of styrenes bearing electron donating and electron withdrawing groups, methylvinyl ketone, and methyl acrylate. The reaction was carried out in an open-flask with 1% mol of palladium acetate in aqueous ethanol at ∼80 °C, giving the correspondent 3-aryl-3,4-dihydroisocoumarins and phthalides with good overall yields. The electronic nature of the group attached to the olefin is a key feature for the regioselectivity of the cyclization step. © 2011 Elsevier Ltd. All rights reserved. 52 48 6342 6345 Nozawa, K., Yamada, M., Tsuda, Y., Kawai, K.I., Nakajima, S., (1981) Chem. Pharm. Bull., 29, pp. 2491-2495 Li, Y., Plitzko, I., Zaugg, J., Hering, S., Hamburger, M., (2010) J. Nat. Prod., 73, pp. 768-770 Cramer, B., Harrer, H., Nakamura, K., Uemura, D., Humpf, H.-U., (2010) Bioorg. Med. Chem., 18, pp. 343-347 Beck, J.J., Chou, S.-C., (2007) J. Nat. Prod., 70, pp. 891-900 Chan, S.S.-K., Choi, A.O.-K., Jones, R.L., Lin, G., (2006) Eur. J. Pharmacol., 537, pp. 111-117 Choi, P.J., Sperry, J., Brimble, M.A., (2010) J. Org. Chem., 75, pp. 7388-7392 Sato, H., Yorozu, H., Yamaoka, S., (1993) Biomed. Res. (Tokyo), 14, pp. 385-390 Barry, R.D., (1964) Chem. Rev., 64, pp. 229-260 Napolitano, E., (1997) Org. Prep. Proced. Int., 29, pp. 631-664 Beak, P., Snieckus, V., (1982) Acc. Chem. Res., 15, pp. 306-312 Joshi, B.S., Jiang, Q.P., Rho, T., Pelletier, S.W., (1994) J. Org. Chem., 59, pp. 8220-8232 Hayat, S., Attaur, R., Choudhary, M.I., Khan, K.M., Bayer, E., (2001) Tetrahedron Lett., 42, pp. 1647-1649 Pedrosa, R., Sayalero, S., Vicente, M., (2006) Tetrahedron, 62, pp. 10400-10407 Fu, P.P., Unruh, L.E., Miller, D.W., Huang, L.W., Yang, D.T.C., (1985) J. Org. Chem., 50, pp. 1259-1261 Fitzgerald, J.J., Pagano, A.R., Sakoda, V.M., Olofson, R.A., (1994) J. Org. Chem., 59, pp. 4117-4121 McNicholas, C., Simpson, T.J., Willett, N.J., (1996) Tetrahedron Lett., 37, pp. 8053-8056 Sharma, A.K., Maheshwary, Y., Singh, P., Singh, K.N., (2010) Arkivoc, pp. 54-62 Watanabe, M., Sahara, M., Kubo, M., Furukawa, S., Billedeau, R.J., Snieckus, V., (1984) J. Org. Chem., 49, pp. 742-747 Broady, S.D., Rexhausen, J.E., Thomas, E.J., (1991) J. Chem. Soc., Chem. Commun., pp. 708-710 Tahara, N., Fukuda, T., Iwao, M., (2004) Tetrahedron Lett., 45, pp. 5117-5120 Clayden, J., Stimson, C.C., Helliwell, M., Keenan, M., (2006) Synlett, pp. 873-876 Shinkaruk, S., Bennetau, B., Babin, P., Schmitter, J.-M., Lamothe, V., Bennetau-Pelissero, C., Urdaci, M.C., (2008) Bioorg. Med. Chem., 16, pp. 9383-9391 Bellinger, G.C.A., Campbell, W.E., Giles, R.G.F., Tobias, J.D., (1982) J. Chem. Soc., Perkin Trans., 1, pp. 2819-2825 Uchiyama, M., Ozawa, H., Takuma, K., Matsumoto, Y., Yonehara, M., Hiroya, K., Sakamoto, T., (2006) Org. Lett., 8, pp. 5517-5520 Landge, S.M., Berryman, M., Török, B., (2008) Tetrahedron Lett., 49, pp. 4505-4508 Günes, M., Speicher, A., (2003) Tetrahedron, 59, pp. 8799-8802 Larock, R.C., Varaprath, S., Lau, H.H., Fellows, C.A., (1984) J. Am. Chem. Soc., 106, pp. 5274-5284 Kundu, N.G., Pal, M., (1993) J. Chem. Soc., Chem. Commun., pp. 86-88 Lee, J.M., Chang, S., (2006) Tetrahedron Lett., 47, pp. 1375-1379 Mandal, S.K., Roy, S.C., (2008) Tetrahedron, 64, pp. 11050-11057 Horino, H., Inoue, N., (1978) Heterocycles, 11, pp. 281-286 Larock, R.C., Yang, H., (1994) Synlett, pp. 748-750 Wu, X., Mahalingam, A.K., Wan, Y., Alterman, M., (2004) Tetrahedron Lett., 45, pp. 4635-4638 Obushak, M.D., Matiychuk, V.S., Turytsya, V.V., (2009) Tetrahedron Lett., 50, pp. 6112-6115 Mizoroki, T., Mori, K., Ozaki, A., (1971) Bull. Chem. Soc. Jpn., 44, p. 581 Heck, R.F., Nolley, J.P., (1972) J. Org. Chem., 37, p. 2320 Kikukawa, K., Matsuda, T., (1977) Chem. Lett., pp. 159-162 Felpin, F.-X., Nassar-Hardy, L., Le Callonnec, F., Fouquet, E., (2011) Tetrahedron, 67, pp. 2815-2831 Taylor, J.G., Moro, A.V., Correia, C.R.D., (2011) Eur. J. Org. Chem., pp. 1403-1428 Zollinger, H., (1994) Diazo Chemistry. Aromatic and Heteroaromatic Compounds, , VCH: Weinheim Criado, A., Gomez-Escalonilla, M.J., Fierro, J.L.G., Urbina, A., Pena, D., Guitian, E., Langa, (2010) F. Chem. Commun. (Cambridge, U. K.), 46, pp. 7028-7030 Okuma, K., Fukuzaki, Y., Nojima, A., Sou, A., Hino, H., Matsunaga, N., Nagahora, N., Yokomori, Y., (2010) Bull. Chem. Soc. Jpn., 83, pp. 1238-1247 Fort, E.H., Scott, L.T., (2011) Tetrahedron Lett., 52, pp. 2051-2053 Malinowski, S., (1952) Rocz. Chem., 26, pp. 85-97 Wang, C., Tan, L.-S., He, J.-P., Hu, H.-W., Xu, J.-H., (2003) Synth. Commun., 33, pp. 773-782 Moro, A.V., Cardoso, F.S.P., Correia, C.R.D., (2008) Tetrahedron Lett., 49, pp. 5668-5671 Teitei, T., (1982) Aust. J. Chem., 35, pp. 1231-1235 Larock, R.C., Hightower, T.R., (1993) J. Org. Chem., 58, pp. 5298-5300 Zeni, G., Larock, R.C., (2004) Chem. Rev., 104, pp. 2285-2309