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Reduction and hydrolysis of substituted 5-oxa-6-azaspiro[2.4]heptane-1,2-dicarboxylic acid esters

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Abstract

Substituted 5-oxa-6-azaspiro[2.4]heptane-1,2-dicarboxylic acid esters synthesized by reaction of nitrones with dimethyl 3-methylidenecyclopropane-1,2-dicarboxylate were reduced with lithium tetrahydridoaluminate to the corresponding bis(hydroxymethyl)cyclopropanes. Alkaline hydrolysis of the title compounds gave substituted cyclopropane-1,2-dicarboxylic acids. In both cases, the 5-oxa-6-azaspiro[2.4]heptane fragment remained intact.

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References

  1. 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; Najera, C. and Sansano, J.M., Org. Biomol. Chem., 2009, vol. 7, p. 4567; Pellisier, H., Tetrahedron, 2010, vol. 66, p. 8341; Cicchi, S., Cordero, F.M., and Giomi, D., Prog. Heterocycl. Chem., 2011, vol. 22, p. 322.

    Google Scholar 

  2. 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.

    Article  CAS  Google Scholar 

  3. Diev, V.V., Tran, T.Q., and Molchanov, A.P., Eur. J. Org. Chem., 2009, p. 525.

  4. 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., Russ. J. Org. Chem., 2011, vol. 47, p. 269; Tran, T.Q., Diev, V.V., Starova, G.L., Gurzhiy, V.V., and Molchanov, A.P., Eur. J. Org. Chem., 2012, p. 2054.

    Article  CAS  Google Scholar 

  5. Hassner, A. and Stumer, C., Organic Syntheses Based on Name Reactions, Amsterdam: Pergamon, 2002, 2nd ed., p. 42; Brandi, A., Guarna, A., Goti, A., and De Sarlo, F., Tetrahedron Lett., 1986, vol. 27, p. 1727.

    Google Scholar 

  6. Ali, S.A. and Wazeer, M.I.M., J. Chem. Soc., Perkin Trans. 1, 1988, p. 597.

  7. Delpierre, G.R. and Lamchen, M., J. Chem. Soc., 1963, p. 4693.

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Authors and Affiliations

  1. St. Petersburg State University, Universitetskii pr. 26, St. Petersburg, 198504, Russia

    A. P. Molchanov & T. Q. Tran

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  1. A. P. Molchanov
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  2. T. Q. Tran
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Correspondence to A. P. Molchanov.

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Original Russian Text © A.P. Molchanov, T.Q. Tran, 2012, published in Zhurnal Organicheskoi Khimii, 2012, Vol. 48, No. 10, pp. 1327–1329.

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Molchanov, A.P., Tran, T.Q. Reduction and hydrolysis of substituted 5-oxa-6-azaspiro[2.4]heptane-1,2-dicarboxylic acid esters. Russ J Org Chem 48, 1323–1325 (2012). https://doi.org/10.1134/S1070428012100107

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  • DOI: https://doi.org/10.1134/S1070428012100107

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