Abstract
Mono-, bi-, tetra-, and pentacyclic N-phthalimidoaziridines with electron-withdrawing substituents in the three-membered ring have been obtained by the oxidative addition of N-aminophthalimide to dimethyl fumarate, ethyl cinnamate, N-phenyl-and N-benzylmaleimide, and endotricyclo[6.2.1.02,7]undeca-4,9-diene-3,6-dione. Photolysis of 3-benzyl-6-phthalimido-3,6-diazabicyclo-[3.1.0]hexane-2,4-dione obtained in this way in the presence of dimethyl acetylenedicarboxylic acid (DMAD) gives in low yield the dimethyl ester of 3-benzyl-2,4-dioxo-8-phthalimido-3,8-diazabicyclo[3.2.1]oct-6-ene-6,7-dicarboxylic acid, the product of 1,3-dipolar cycloaddition to the N-phthalimidoazomethinylide formed as intermediate. However photolysis of this phthalimidoaziridine in the presence of other 1,3-dipolarophiles, like photolysis in the presence of DMAD of the remaining phalimidoaziridines, does not lead to a 1,3-dipolar cycloaddition product.
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References
J. W. Lown, in: A. Padwa (editor), 1,3-Dipolar Cycloaddition Chemistry, Wiley-Interscience, New York (1984), p. 653.
P. Garner, W. B. Ho, S. K. Grandhee, W. S. Youngs, and V. O. Kennedy, J. Org. Chem., 56, 5893 (1991).
L. M. Harwood and R. J. Vickers, in: A. Padwa and W. H. Pearson (editors), Chemistry of Heterocyclic Compounds. Vol. 59, Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry toward Heterocycles and Natural Products, Wiley-Interscience, New York (2002), p. 169.
H. Person, K. Luanglath, M. Baudru, and A. Foucaud, Bull. Soc. Chim. France, 1989 (1976).
F. Texier-Boullet and A. Foucaud, Tetrahedron Lett., 23, 4927 (1982).
J. Charrier, A. Foucaud, H. Person, and E. Loukakou, J. Org. Chem., 48, 481 (1983).
T. L. Gilchrist, C. W. Rees, and E. Stanton, J. Chem. Soc., C, 988 (1971).
P. Marchand and R. W. Allen, J. Org. Chem., 39, 1596 (1974).
P. Yates and K. Switlak, Can. J. Chem., 68, 1894 (1990).
M. A. Kuznetsov and B. V. Ioffe, Usp. Khim., 58, 1271 (1989).
R. S. Atkinson, E. Barker, C. K. Meades, and H. A. Albar, J. Chem. Soc., Chem. Commun., 29 (1998).
R. S. Atkinson, Tetrahedron, 55, 1519 (1999).
T. Siu and A. K. Yudin, J. Am. Chem. Soc., 124, 530 (2002).
V. V. Semenovskii, Dissertation for Candidate of Chemical Sciences, Leningrad State University (LGU), Leningrad (1991).
L. Hoesch, N. Egger, and A. S. Dreiding, Helv. Chim. Acta, 61, 795 (1972).
R. S. Atkinson and J. R. Malpass, J. Chem. Soc., Perkin Trans. 1, 2242 (1977).
Y. Tamuru, H. Harayama, H. Sakata, H. Konishi, K. Fugami, M. Kimura, S. Tanaka, T. Okajima, and Y. Fakudzava, Liebigs Ann. Recl., 907 (1997).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1320–1328, September, 2006.
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Kuznetsov, M.A., Ushkov, A.V., Selivanov, S.I. et al. Synthesis and photolysis of N-phthalimidoaziridines with electron-withdrawing substituents. Chem Heterocycl Compd 42, 1143–1150 (2006). https://doi.org/10.1007/s10593-006-0218-8
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DOI: https://doi.org/10.1007/s10593-006-0218-8