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Synthesis of 8-oxa-2-azaspiro[4.5]decane

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Abstract

A convenient synthesis of new 8-oxa-2-azaspiro[4.5]decane from commercially available reagents based on tetrahydropyran-4-carbonitrile and 1-bromo-2-fluoroethane has been developed. This compound is promising for the production of important biologically active compounds.

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References

  1. R. Rios, Chem. Soc. Rev., 2012, 41, 1060.

    CAS  Google Scholar 

  2. A. S. Ding, M. Meazza, H. Guo, J. W. Yang, R. Rios, Chem. Soc. Rev., 2018, 47, 5946.

    CAS  Google Scholar 

  3. A. Yu. Barkov, N. S. Zimnitskiy, I. B. Kutyashev, V. Yu. Korotaev, V. Ya. Sosnovskikh, Chem. Heterocycl. Compd. (Engl. Transl.), 2018, 54, 43.

    CAS  Google Scholar 

  4. L M. Saliyeva, N. Yu. Slyvka, D. A. Mel’nyk, E. B. Rusanov, R. I. Vas’kevich, M. V. Vovk, Chem. Heterocycl. Compd. (Engl. Transl.), 2018, 54, 130.

    CAS  Google Scholar 

  5. I. B. Kutyashev, A. Yu. Barkov, V. Yu. Korotaev, V. Ya. Sosnovskikh, Chem. Heterocycl. Compd. (Engl. Transl.), 2019, 55, 529.

    CAS  Google Scholar 

  6. I. B. Kutyashev, A. Yu. Barkov, N. S. Zimnitskiy, V. Yu. Korotaev, V. Ya. Sosnovskikh, Chem. Heterocycl. Compd. (Engl. Transl.), 2019, 55, 861.

    CAS  Google Scholar 

  7. V. Yu. Korotaev, N. S. Zimnitskiy, A. Yu. Barkov, I. B. Kutyashev, V. Ya. Sosnovskikh, Chem. Heterocycl. Compd. (Engl. Transl.), 2018, 54, 905.

    CAS  Google Scholar 

  8. E. V. Suslov, K. Yu. Ponomarev, D. V. Korchagina, K. P. Volcho, N. F. Salakhutdinov, Russ. Chem. Bull., 2019, 68, 601.

    CAS  Google Scholar 

  9. V. D. Gvozdev, K. N. Shavrin, O. M. Nefedov, Russ. Chem. Bull., 2019, 68, 2108.

    CAS  Google Scholar 

  10. J. Gunzner-Toste, G. Zhao, P. Bauer, T. Baumeister, A. J. Buckmelter, M. Caligiuri, K. H. Clodfelter, B. Fu, B. Han, Y.-C. Ho, N. Kley, X. Liang, B. M. Liederer, J. Lin, S. Mukadam, T. O’Brien, A. Oh, D. J. Reynolds, G. Sharma, N. Skelton, C. C. Smith, J. Sodhi, W. Wanga, Z. Wang, Y. Xiao, P.-w. Yuen, M. Zak, L. Zhang, X. Zheng, K. W. Bair, P. S. Dragovich, Bioorg. Med. Chem. Lett., 2013, 23, 3531.

    CAS  Google Scholar 

  11. K. Weinberg, A. Stoit, C. G. Kruse, M. F. Haddowa, T. Gallagher, Tetrahedron Lett., 2013, 69, 4694.

    CAS  Google Scholar 

  12. C. G. Overberger, D. W. Wang, R. K. Hill, G. R. Krow, D. W. Ladner, J. Org. Chem., 1981, 46, 2757.

    CAS  Google Scholar 

  13. Z. Cheng, X. Han, M. Jiang, J. Wang, Y. Wang, S. Yang, Pat. WO2018/19521, 2018.

  14. W. Yong, Z. Liwen, W. Zhanguo, J. Jianfeng, D. Peng, L. Kunzhi, W. Dongdong, W. Hui, T. Ying, Pat. CN109422760, 2019.

  15. A. Casimiro-Garcia, J. W. Strohbach, D. Hepworth, F. E. Lovering, C. Choi, C. P. Allais, S. W. Wright, Pat. WO2018/11681, 2018.

  16. L. Hirvelä, M. Hakola, T. Linnanen, P. Koskimies, C. Stjernschantz, Pat. WO2018/224736, 2018.

  17. T. Akai, J. Moore, N. R. Perl, R. R. Iyengar, A. Mermerian, G-Y. J. Im, T. W.-H. Lee, T. C. Hudson, G. R. Rennie, J. Jia, P. A. Renhowe, T. C. Barden, X. Y. Yu, J. E. Sheppeck, K. Iyer, J. Jung, Pat. WO2014/144100, 2014.

  18. N. Galapagos, N. Desroy, B. Heckmann, R. C. X. Brys, A. M. Joncour, C. Peixoto, X. M. Bock, C. G. Housseman, Pat. WO2014/202458, 2014.

  19. B. Mathys, C. Müller, M. Scherz, T. Weller, M. Clozel, J. Velker, D. Bur, Pat. WO2005/30209, 2005.

  20. Q. Tang, M. Xu, S.-H. Chen, G. Li, Synth. Commun., 2007, 37, 3793.

    CAS  Google Scholar 

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Correspondence to O. A. Rakitin.

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Russian Chemical Bulletin, International Edition, Vol. 69, No. 10, pp. 2017–2019, October, 2020

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2017–2019, October, 2020.

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Ogurtsov, V.A., Rakitin, O.A. Synthesis of 8-oxa-2-azaspiro[4.5]decane. Russ Chem Bull 69, 2017–2019 (2020). https://doi.org/10.1007/s11172-020-2994-1

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  • DOI: https://doi.org/10.1007/s11172-020-2994-1

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