Abstract
C-Aryl- and C-carbamoylnitrones reacted with methyl 2-benzylidenecyclopropanecarboxylate in highly regioselective fashion to give the corresponding 1,3-dipolar cycloaddition products, substituted methyl 5-oxa-6-azaspiro[2.4]heptane-1-carboxylates as mixtures of two diastereoisomers.
Similar content being viewed by others
References
Tufarielo, J.J., 1,3-Dipolar Cycloaddition Chemistry, Padwa, A., Ed., New York: Wiley, 1984; Jones, R.C.F. and Martin, J.N., Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry toward Heterocycles and Natural Products, Padwa, A. and Pearson, W.H., Eds., New York: Wiley, 2002, p. 1; Grigor’ev, I.A., Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis, Feuer, H., Ed., Hoboken, NJ: Wiley, 2007, p. 129.
Brandi, A. and Goti, A., Chem. Rev., 1998, vol. 98, p. 589; Brandi, A., Cicchi, S., Cordero, F.M., and Goti, A., Chem. Rev., 2003, vol. 103, p. 1213; Goti, A., Cordero, F.M., and Brandi, A., Top. Curr. Chem., 1996, vol. 178, p. 1; Diev, V.V., Stetsenko, O.N., Tran, T.Q., Kopf, J., Kostikov, R.R., and Molchanov, A.P., J. Org. Chem., 2008, vol. 73, p. 2396.
Diev, V.V., Tran, T.Q., and Molchanov, A.P., Eur. J. Org. Chem., 2009, p. 525; Tran, T.Q., Diev, V.V., and Molchanov, A.P., Tetrahedron, 2011, vol. 67, p. 2391; Molchanov, A.P., Tran, T.Q., and Kostikov, R.R., Izv. Ross. Akad. Nauk, Ser. Khim., 2011, p. 2253.
Tran, T.Q., Diev, V.V., Starova, G.L., Gurzhiy, V.V., and Molchanov, A.P., Eur. J. Org. Chem., 2012, p. 2054.
Svetkin, Yu.V., Akmanova, N.A., and Karataeva, G.I., Zh. Org. Khim., 1972, vol. 8, p. 2431; Akmanova, N.A., Sagitdinova, Kh.F., and Balenkova, E.S., Khim. Geterotsikl. Soedin., 1982, p. 1192; Andrade, M.M., Barros, M.T., and Pinto, R.C., Tetrahedron, 2008, vol. 64, p. 10 521; Molchanov, A.P., Tran, T.Q., and Kostikov, R.R., Russ. J. Org. Chem., 2011, vol. 47, p. 269.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © A.P. Molchanov, T.Q. Tran, 2012, published in Zhurnal Organicheskoi Khimii, 2012, Vol. 48, No. 10, pp. 1289–1294.
Rights and permissions
About this article
Cite this article
Molchanov, A.P., Tran, T.Q. Regioselective cycloaddition of C-aryl- and C-carbamoylnitrones to methyl 2-benzylidenecyclopropanecarboxylate. Russ J Org Chem 48, 1283–1288 (2012). https://doi.org/10.1134/S1070428012100041
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428012100041