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Synthesis of N-Substituted Tetra(hexa)oxazaspiroalkanes Using Amino Acids and Samarium Catalysts

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Abstract

An efficient procedure has been developed for the synthesis of N-substituted tetra(hexa)oxazaspiroalkanes by reaction of heptaoxadispiroalkanes and pentaoxaspiroalkanes with amino acids (glycine, alanine, leucine, valine, methionine) in the presence of samarium-containing catalysts.

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REFERENCES

  1. Makhmudiyarova, N.N., Khatmullina, G.M., Rakhimov, R.Sh., Meshcheryakova, E.S., Ibragimov, A.G., and Dzhemilev, U.M., Tetrahedron, 2016, vol. 72, p. 3277. https://doi.org/10.1016/j.tet.2016.04.055

    Article  CAS  Google Scholar 

  2. Tyumkina, T.V., Makhmudiyarova, N.N., Kiyamutdinova, G.M., Meshcheryakova, E.S., Bikmukhametov, K.Sh., Abdullin, M.F., Khalilov, L.M., Ibragimov, A.G., and Dzhemilev, U.M., Tetrahedron, 2018, vol. 74, p. 1749. https://doi.org/10.1016/j.tet.2018.01.045

    Article  CAS  Google Scholar 

  3. Makhmudiyarova, N.N., Rakhimov, R.Sh., Tyumkina, T.V., Meshcheryakova, E.S., Ibragimov, A.G., and Dzhemilev, U.M., Russ. J. Org. Chem., 2019, vol. 55, p. 620. https://doi.org/10.1134/S1070428019050075

    Article  CAS  Google Scholar 

  4. Makhmudiyarova, N.N., Ishmukhametova, I.R., Tyumkina, T.V., Ibragimov, A.G., and Dzhemilev, U.M., Tetrahedron Lett., 2018, vol. 59, p. 3161. https://doi.org/10.1016/j.tetlet.2018.07.010

    Article  CAS  Google Scholar 

  5. Makhmudiyarova, N.N., Ishmukhametova, I.R., Dzhemileva, L.U., Tyumkina, T.V., D’yakonov, V.A., Ibragimov, A.G., and Dzhemilev, U.M., RSC Adv., 2019, vol. 9, p. 18923. https://doi.org/10.1039/C9RA02950H

    Article  CAS  Google Scholar 

  6. Makhmudiyarova, N.N., Koroleva, L.S., Meshcheryakova, E.S., and Ibragimov, A.G., Russ. J. Org. Chem., 2020, vol. 56, p. 378. https://doi.org/10.31857/S0514749220030027

    Article  CAS  Google Scholar 

  7. Makhmudiyarova, N.N., Shangaraev, K.R., Dzhemileva, L.U., Tuymkina, T.V., Mescheryakova, E.S., D’yakonov, V.A., Ibragimov, A.G., and Dzhemilev, U.M., RSC Adv., 2019, vol. 9, p. 29949. https://doi.org/10.1039/c9ra06372b

    Article  CAS  Google Scholar 

  8. Cremer, D. and Pople, J.A., J. Am. Chem. Soc., 1975, vol. 97, p. 1354. https://doi.org/10.1021/ja00839a011

    Article  CAS  Google Scholar 

  9. Makhmudiyarova, N.N., Khatmullina, G.M., Rakhimov, R.Sh., Ibragimov, A.G., and Dzhemilev, U.M., Arkivoc, 2016, vol. 2016, part (v), p. 427. https://doi.org/10.24820/ark.5550190.p009.565

    Article  Google Scholar 

  10. CrysAlis PRO, Yarnton, Oxfordshire, England: Agilent Tecnologies, 2012.

  11. Sheldrick, G.M., Acta Crystallogr., Sect. A, 2015, vol. 71, p. 3. https://doi.org/10.1107/S2053273314026370

    Article  CAS  Google Scholar 

  12. Sheldrick, G.M., Acta Crystallogr., Sect. C, 2015, vol. 71, p. 3. https://doi.org/10.1107/S2053229614024218

    Article  CAS  Google Scholar 

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ACKNOWLEDGMENTS

Structural studies were carried out at the Agidel joint center, Institute of Petrochemistry and Catalysis, Russian Academy of Sciences.

Funding

This study was performed under financial support by the Russian Foundation for Basic Research (project no. 20-30-90002).

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Correspondence to N. N. Makhmudiyarova.

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Makhmudiyarova, N.N., Ishmukhametova, I.R., Shangaraev, K.R. et al. Synthesis of N-Substituted Tetra(hexa)oxazaspiroalkanes Using Amino Acids and Samarium Catalysts. Russ J Org Chem 57, 64–70 (2021). https://doi.org/10.1134/S1070428021010097

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  • DOI: https://doi.org/10.1134/S1070428021010097

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