Artículos de revistas
Arylation Of β,γ-unsaturated Lactones By A Heck-matsuda Reaction: An Unexpected Route To Aryldiazene Butenolides And Pyridazinones
Registro en:
Quimica Nova. , v. 33, n. 10, p. 2070 - 2074, 2010.
1004042
2-s2.0-78650532235
Autor
Taylor J.G.
Correia C.R.D.
Institución
Resumen
The palladium catalysed coupling of aryldiazonium salts with β-γ-unsaturated lactones under basic conditions has been investigated. Both (3H)-furanone and α-angelicalactone were evaluated as substrates in the Heck Matsuda reaction but both failed to afford the desired arylated butenolides. Under basic conditions, β-γ-unsaturated lactones generate highly nucleophilic enolates that preferentially undergo azo coupling reactions with arenediazonium salts to afford aryldiazene butenolides. The electronic and steric effect of the substituents on the aryldiazonium salt in the azo coupling reaction is described. Aryldiazene-lactone derivatives were obtained in good yields from a highly facile and straightforward procedure. An aminoisomaleimide was formed from (3H)-furanone and cyclised to the corresponding pyridazinones in modest yield. 33 10 2070 2074 Tsuji, J., (1997) Palladium Reagents and Catalysts: Innovations in Organic Synthesis, , 1st ed., Wiley: London Shibasaki, M., Vogl, E.M., Ohshima, T., (2004) Adv. Synth. Catal., 346, p. 1533. , For reviews see Dounay, A.B., Overman, L.E., (2003) Chem. Rev., 103, p. 2945 Siqueira, F.A., Taylor, J.G., Correia, C.R.D., (2010) Tetrahedron. Lett., 51, p. 2102. , For selected examples see Moro, A.V., Cardoso, F.S.P., Correia, C.R.D., (2009) Org. Lett., 11, p. 3642 Pastre, J.C., Correia, C.R.D., (2009) Adv. Synth. Catal., 351, p. 1217 Machado, A.H.L., De Sousa, M.A., Patto, D.C.S., Azevedo, L.F.S., Bombonato, F.I., Correia, C.R.D., (2009) Tetrahedron. Lett., 50, p. 1222 Moro, A.V., Cardoso, F.S.P., Correia, C.R.D., (2008) Tetrahedron. Lett., 49, p. 5668 Coy, E.D., Jovanovic, L., Sefkow, M., (2010) Org. Lett., 12, p. 1976. , For selected examples see Cacchi, S., Fabrizi, G., Goggiamani, A., Sferrazza, A., (2009) Synlett, 8, p. 1277 Bartoli, G., Cacchi, S., Fabrizi, G., Goggiamani, A., (2008) Synlett, 16, p. 2508 Barbero, M., Cadamuro, S., Dughera, S., (2006) Synthesis, 20, p. 3443 Kikukawa, K., Matsuda, T., (1977) Chem. Lett., p. 159 Sengupta, S., Bhattacharyya, S., (2001) Tetrahedron. Lett., 42, p. 2035 Kikukawa, K., Nagira, K., Wada, F., Matsuda, T., (1981) Tetrahedron., 37, p. 31 Kikukawa, K., Matsuda, T., (1977) Chem. Lett., p. 159 Hyde, A.M., Buchwald, S.L., (2009) Org. Lett., 11, p. 2663 Szele, I., Zollinger, H., (1983) Top. Curr. Chem., 112, p. 1 Otto, D., (1907) Berichte der Deutschen Chemischen Gesellschaft, 40, p. 2404 Shapiro, D., Segal, H., Flowers, H.M., (1958) J. Am. Chem., 80, p. 1194. , For examples see Venturello, C., D'Aloisio, R., (1979) Synthesis, 4, p. 283 Garst, M.E., Lukton, D., (1980) Synth. Commun., 10, p. 155 Blank, O., Wetzel, A., Ullrich, D., Heinrich, M.R., (2008) Eur. J. Org. Chem., 18, p. 3179 Jackson, A., Joule, J.A., (1967) Chem. Commun., 9, p. 459. , For examples see Shawali, A.S., El-Galil, A.M., (1971) Tetrahedron., 27, p. 4305 Bestmann, H.J., Schmid, G., Sandmeier, D., (1980) Tetrahedron. Lett., 21, p. 2939 Atlan, V., Kaim, L., Supiot, C., (2000) Chem. Commun., 15, p. 1385 Tsou, K.C., Barnett, R.J., Seligman, A.M., (1955) J. Am. Chem. Soc., 77, p. 4613. , first aminoisomaleimide synthesis was reported in 1955 by Tsou and formed by intramolecular condensation of an N-substituted maleamic acid using trifuroacetic anhydride as dehydrating agent Naesman, J.A.H., Pensar, K.G., (1985) Synthesis, 8, p. 786 Kraus, G.A., Roth, B., (1977) Tetrahedron. Lett., 18, p. 3129. , Dimerisation and polymerisation of butenolides has been previously reported Parnarouskis, M., Rubinstein, H., (1976) J. Heterocycl. Chem., 13, p. 423 Meier, K.D., Ringier, B.H., Druey, J., (1954) Helv. Chim. Acta, 37, p. 523 Seymour, D., (1955) J. Chem. Soc., p. 852 Baloniak, S., Mroczkiewicz, A., Katrusiak, A., (1996) Pol. J. Chem., 70, p. 1274 Tartar, A., Melnyk, P., (1996) Tetrahedron. Lett., 37, p. 4145 Conley, N.R., Hung, R.J., Willson, C.G., (2005) J. Org. Chem., 70, p. 4553 Johnston, A.K., Allcock, R.W., Jiang, Z., Collier, I.D., Blakli, H., Rosair, G.M., Bailey, P.D., Adams, D.R., (2008) Org. Biomol. Chem., 6, p. 175 Natarajan, S.R., Heller, S.T., Nam, K., Singh, S.B., Scapin, G., Patel, S., Thompson, J.E., O'Keefe, S.J., (2006) Bioorg. Med. Chem. Lett., 16, p. 5809 Dal Piaz, P., Vergelli, C., Castellana, M.C., Gioavannoni, M.P., Pieretti, S., (2002) J. Heterocycl. Chem., 39, p. 523 Matyus, P., (1998) J. Heterocycl. Chem., 35, p. 1075 Jones, J.B., Barker, J.N., (1970) Can. J. Chem., 48, p. 1574. , This reaction is known to occur under basic conditions Lukes, R., Syhora, K., (1954) Collect. Czech. Chem. Commun., 19, p. 1205 David, P., Langlois, H.W., (1948) J. Am. Chem. Soc., 70, p. 2624 Herbst, W., Hunger, K., (1978) Prog. Org. Coat, 6, p. 105