Cleavage of the N-O Bond in the 4-Spirocyclopropaneisoxazolidine Carboxylate and Subsequent Cycloaddition
Main Article Content
Abstract
1. 3 Dipolar cycloaddition of nitrones to the double carbon carbon bond of acceptor ring substituted methylenecyclopropanes affords thermally stable regioisomeric 4 spirocyclopropaneisoxazolidine. Cleavage of the N - O bond in 4-spirocyclopropaneisoxazolidine with ester groups on the three - membered ring by the action of activated zinc dust in acetic acid gives the corespoding 1, 3-amino ancohols containing cyclopropyl ring, whose subsequent cyclization under the reaction conditions yield bi- or tricyclic lactams or lactones with retention of the three membered ring structural moieties of antibiotics and biologically active compounds.
Keywords
4-spirocyclopropaneisoxazolidine carboxylate, 1,3-amino alcohols, lactones, cleavage of the N-O bond
Article Details
References
[1]. A. Hassner, I. Namboothiri, Organic Syntheses based on Name Reactions; Pergamon, Elsevier (2012) p. 60. (b) A. Brandi, A. Guarna, A. Goti, F. De Sarlo, Tetrahedron Lett. (1986) 27, 1727.
[2]. A. Brandi, S. Garro, A. Guarna, A. Goti, F. Cordero, F. De Sarlo, J. Org. Chem. (1988), 53, 2430. (b) F. M. Cordero, A. Goti, F. De Sarlo, A. Guarna, A. Brandi, Tetrahedron. (1989), 45, 5917. (c) A. Brandi, Y. Durust, F. M. Cordero, F. De Sarlo, J. Org. Chem. (1992), 57, 5666. (d) F. M. Cordero, A. Brandi, C. Querci, A. Goti, F. De Sarlo, A. Guarna, J. Org. Chem. (1990), 55, 1762. (e) A. Brandi, F. M. Cordero, F. De Sarlo, A. Goti, A. Guarna, Synlett. (1993), 1. (f) F. M. Cordero. F. De Sarlo, A. Brandi, Monatsh. Chem. (2004), 135, 649.
[3]. Diev V.V., Tran Q.T., Molchanov A. P. Eur. J. Org. Chem. (2009), 525; b) T. Q. Tran, V. V. Diev, A. P. Molchanov, Tetrahedron (2011), 67, 2391. c) A. P. Molchanov, T. Q. Tran, R. R. Kostikov, Russ. J. Org. Chem. (2011), 47, 269; d) A. P. Molchanov, T. Q. Tran, Russ. J. Org. Chem. (2012), 48, 1283; e) A. P. Molchanov, T. Q. Tran, Chem. Heterocycl. Comp. (2013), 49, 479; f) A.P. Molchanov, T.Q. Tran, A.V. Stepakov, G.L.Starova, R.R. Kostikov, Russ. J. Org. Chem. (2014), 50, 78.
[4]. Tran T.Q., Diev V.V., Starova G. L., Gurzhiy V.V., Molchanov A.P. Eur. J. Org. Chem. (2012), 2054
[5]. Huisgen R., Hauck H., Grashey R., Seidl H. Chem. Ber. (1968), 101, 2568; b) Huisgen R., Hauck H., Grashey R., Seidl H. Chem. Ber. (1969), 102, 736; c) LeBel N. A., Post M. E., Whang J. J. J. Am. Chem.. Soc. (1964), 86, 3759.
[6]. Budzinska A., Sas W. Tetrahedron, (2001), 57, 2021-2030; b) Tice C. M., Ganem B. J. Org. Chem. (1983), 48, 5048-5050; c) Chiacchio U., Piperno A., Rescifina A., Romeo G., Uccella N. Tetrahedron, (1998), 54, 5695-5708; d) LeBel N. A., Post M. E., Whang J. J. J. Am. Chem.. Soc. (1964), 86, 3759; e) Tice C. M., Ganem B. J. Org. Chem. (1983), 48, 5048.
[7]. Merino P., Mates J.A., Revuelta J., Tejero T., Chiacchio U., Romeo G., Iannazzo D., Romeo R. Tetrahedron: Asymmetry, (2002), 13, 173; b) Cordero F.M., Pisaneschi F., Batista K.M., Valenza S., Machetti F., Brandi A. J. Org. Chem., (2005), 70, 3, 856.
[8]. Cicchi S., Goti A., Brandi A., Guarna A.. De Sarlo F. Tetrahedron Lett. (1990), 31, 3351; b) F. Pisaneschi, C. Della Monica, F. M. Cordero. A. Brandi, Tetrahedron Lett. (2002), 43, 5711.
[9]. S. Cicchi, J. Revuelta, A. Zanobini, M. Betti, A. Brandi Synlett, (2003), 2305.
[10]. Revuelta, J.; Cicchi, S.; Brandi, A. Tetrahedron Lett. (2004), 45, 8375.
[11]. Molchanov A.P., Tran T.Q., Stepakov A.V., Kostikov R.R. Russ. J. Org. Chem. (2016), 52, 404.
[2]. A. Brandi, S. Garro, A. Guarna, A. Goti, F. Cordero, F. De Sarlo, J. Org. Chem. (1988), 53, 2430. (b) F. M. Cordero, A. Goti, F. De Sarlo, A. Guarna, A. Brandi, Tetrahedron. (1989), 45, 5917. (c) A. Brandi, Y. Durust, F. M. Cordero, F. De Sarlo, J. Org. Chem. (1992), 57, 5666. (d) F. M. Cordero, A. Brandi, C. Querci, A. Goti, F. De Sarlo, A. Guarna, J. Org. Chem. (1990), 55, 1762. (e) A. Brandi, F. M. Cordero, F. De Sarlo, A. Goti, A. Guarna, Synlett. (1993), 1. (f) F. M. Cordero. F. De Sarlo, A. Brandi, Monatsh. Chem. (2004), 135, 649.
[3]. Diev V.V., Tran Q.T., Molchanov A. P. Eur. J. Org. Chem. (2009), 525; b) T. Q. Tran, V. V. Diev, A. P. Molchanov, Tetrahedron (2011), 67, 2391. c) A. P. Molchanov, T. Q. Tran, R. R. Kostikov, Russ. J. Org. Chem. (2011), 47, 269; d) A. P. Molchanov, T. Q. Tran, Russ. J. Org. Chem. (2012), 48, 1283; e) A. P. Molchanov, T. Q. Tran, Chem. Heterocycl. Comp. (2013), 49, 479; f) A.P. Molchanov, T.Q. Tran, A.V. Stepakov, G.L.Starova, R.R. Kostikov, Russ. J. Org. Chem. (2014), 50, 78.
[4]. Tran T.Q., Diev V.V., Starova G. L., Gurzhiy V.V., Molchanov A.P. Eur. J. Org. Chem. (2012), 2054
[5]. Huisgen R., Hauck H., Grashey R., Seidl H. Chem. Ber. (1968), 101, 2568; b) Huisgen R., Hauck H., Grashey R., Seidl H. Chem. Ber. (1969), 102, 736; c) LeBel N. A., Post M. E., Whang J. J. J. Am. Chem.. Soc. (1964), 86, 3759.
[6]. Budzinska A., Sas W. Tetrahedron, (2001), 57, 2021-2030; b) Tice C. M., Ganem B. J. Org. Chem. (1983), 48, 5048-5050; c) Chiacchio U., Piperno A., Rescifina A., Romeo G., Uccella N. Tetrahedron, (1998), 54, 5695-5708; d) LeBel N. A., Post M. E., Whang J. J. J. Am. Chem.. Soc. (1964), 86, 3759; e) Tice C. M., Ganem B. J. Org. Chem. (1983), 48, 5048.
[7]. Merino P., Mates J.A., Revuelta J., Tejero T., Chiacchio U., Romeo G., Iannazzo D., Romeo R. Tetrahedron: Asymmetry, (2002), 13, 173; b) Cordero F.M., Pisaneschi F., Batista K.M., Valenza S., Machetti F., Brandi A. J. Org. Chem., (2005), 70, 3, 856.
[8]. Cicchi S., Goti A., Brandi A., Guarna A.. De Sarlo F. Tetrahedron Lett. (1990), 31, 3351; b) F. Pisaneschi, C. Della Monica, F. M. Cordero. A. Brandi, Tetrahedron Lett. (2002), 43, 5711.
[9]. S. Cicchi, J. Revuelta, A. Zanobini, M. Betti, A. Brandi Synlett, (2003), 2305.
[10]. Revuelta, J.; Cicchi, S.; Brandi, A. Tetrahedron Lett. (2004), 45, 8375.
[11]. Molchanov A.P., Tran T.Q., Stepakov A.V., Kostikov R.R. Russ. J. Org. Chem. (2016), 52, 404.