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.331020702074Tsuji, J., (1997) Palladium Reagents and Catalysts: Innovations in Organic Synthesis, , 1st ed., Wiley: LondonShibasaki, M., Vogl, E.M., Ohshima, T., (2004) Adv. Synth. Catal., 346, p. 1533. , For reviews seeDounay, A.B., Overman, L.E., (2003) Chem. Rev., 103, p. 2945Siqueira, F.A., Taylor, J.G., Correia, C.R.D., (2010) Tetrahedron. Lett., 51, p. 2102. , For selected examples seeMoro, A.V., Cardoso, F.S.P., Correia, C.R.D., (2009) Org. Lett., 11, p. 3642Pastre, J.C., Correia, C.R.D., (2009) Adv. Synth. Catal., 351, p. 1217Machado, 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. 1222Moro, A.V., Cardoso, F.S.P., Correia, C.R.D., (2008) Tetrahedron. Lett., 49, p. 5668Coy, E.D., Jovanovic, L., Sefkow, M., (2010) Org. Lett., 12, p. 1976. , For selected examples seeCacchi, S., Fabrizi, G., Goggiamani, A., Sferrazza, A., (2009) Synlett, 8, p. 1277Bartoli, G., Cacchi, S., Fabrizi, G., Goggiamani, A., (2008) Synlett, 16, p. 2508Barbero, M., Cadamuro, S., Dughera, S., (2006) Synthesis, 20, p. 3443Kikukawa, K., Matsuda, T., (1977) Chem. Lett., p. 159Sengupta, S., Bhattacharyya, S., (2001) Tetrahedron. Lett., 42, p. 2035Kikukawa, K., Nagira, K., Wada, F., Matsuda, T., (1981) Tetrahedron., 37, p. 31Kikukawa, K., Matsuda, T., (1977) Chem. Lett., p. 159Hyde, A.M., Buchwald, S.L., (2009) Org. Lett., 11, p. 2663Szele, I., Zollinger, H., (1983) Top. Curr. Chem., 112, p. 1Otto, D., (1907) Berichte der Deutschen Chemischen Gesellschaft, 40, p. 2404Shapiro, D., Segal, H., Flowers, H.M., (1958) J. Am. Chem., 80, p. 1194. , For examples seeVenturello, C., D'Aloisio, R., (1979) Synthesis, 4, p. 283Garst, M.E., Lukton, D., (1980) Synth. Commun., 10, p. 155Blank, O., Wetzel, A., Ullrich, D., Heinrich, M.R., (2008) Eur. J. Org. Chem., 18, p. 3179Jackson, A., Joule, J.A., (1967) Chem. Commun., 9, p. 459. , For examples seeShawali, A.S., El-Galil, A.M., (1971) Tetrahedron., 27, p. 4305Bestmann, H.J., Schmid, G., Sandmeier, D., (1980) Tetrahedron. Lett., 21, p. 2939Atlan, V., Kaim, L., Supiot, C., (2000) Chem. Commun., 15, p. 1385Tsou, 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 agentNaesman, J.A.H., Pensar, K.G., (1985) Synthesis, 8, p. 786Kraus, G.A., Roth, B., (1977) Tetrahedron. Lett., 18, p. 3129. , Dimerisation and polymerisation of butenolides has been previously reportedParnarouskis, M., Rubinstein, H., (1976) J. Heterocycl. Chem., 13, p. 423Meier, K.D., Ringier, B.H., Druey, J., (1954) Helv. Chim. Acta, 37, p. 523Seymour, D., (1955) J. Chem. Soc., p. 852Baloniak, S., Mroczkiewicz, A., Katrusiak, A., (1996) Pol. J. Chem., 70, p. 1274Tartar, A., Melnyk, P., (1996) Tetrahedron. Lett., 37, p. 4145Conley, N.R., Hung, R.J., Willson, C.G., (2005) J. Org. Chem., 70, p. 4553Johnston, 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. 175Natarajan, 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. 5809Dal Piaz, P., Vergelli, C., Castellana, M.C., Gioavannoni, M.P., Pieretti, S., (2002) J. Heterocycl. Chem., 39, p. 523Matyus, P., (1998) J. Heterocycl. Chem., 35, p. 1075Jones, J.B., Barker, J.N., (1970) Can. J. Chem., 48, p. 1574. , This reaction is known to occur under basic conditionsLukes, R., Syhora, K., (1954) Collect. Czech. Chem. Commun., 19, p. 1205David, P., Langlois, H.W., (1948) J. Am. Chem. Soc., 70, p. 2624Herbst, W., Hunger, K., (1978) Prog. Org. Coat, 6, p. 10
