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Synthesis of spirocyclic pyrrolidines from cyclopentylideneacetic acid derivatives

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Chemistry of Heterocyclic Compounds Aims and scope

A simple method for the synthesis of 2-benzylazaspiro[4.4]nonanes via the reaction of low reactivity ethylidenecyclopentane derivatives with N-benzyl azomethine ylide obtained in situ was proposed.

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References

  1. Burkhard, J. A.; Wagner, B.; Fischer, H.; Schuler, F.; Müller, K.; Carreira, E. M. Angew. Chem., Int. Ed. 2010, 49, 3524.

    Article  CAS  Google Scholar 

  2. Lovering, F.; Bikker, J.; Humblet, C. J. Med. Chem. 2009, 52, 6752.

    Article  CAS  PubMed  Google Scholar 

  3. Undheim, K. Synthesis 2015, 2497.

  4. Geoghegan, K.; Bode, J. W. Org. Lett. 2015, 17, 1934.

    Article  CAS  PubMed  Google Scholar 

  5. Perry M. A.; Hill, R. R. ; Leong, J. J.; Rychnovsky, S. D. Org. Lett. 2015, 17, 3268.

    Article  CAS  PubMed  Google Scholar 

  6. Kumar, S.; Thornton, P. D.; Painter, T. O.; Jain, P. ; Downard, J.; Douglas, J. T.; Santini, C. J. Org. Chem. 2013, 78, 6529.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  7. Chalyk, B. A.; Butko, M. V.; Yanshyna, O. O.; Gavrilenko, K. S.; Druzhenko, T. V.; Mykhailiuk, P. K. Chem.–Eur. J. 2017, 23, 16782.

    Article  CAS  PubMed  Google Scholar 

  8. Laborde, E. Tetrahedron Lett. 1992, 33, 6607.

    Article  CAS  Google Scholar 

  9. Orlek, B. S.; Wadsworth, H.; Wyman, P.; Hadley, M. S. Tetrahedron Lett. 1991, 32, 1241.

    Article  CAS  Google Scholar 

  10. Brindani, N.; Rassu, G.; Dell'Amico, L.; Zambrano, V.; Pinna, L.; Curti, C.; Sartori, A.; Battistini, L.; Casiraghi, G.; Pelosi, G.; Greco, D.; Zanardi, F. Angew. Chem., Int. Ed. 2015, 54, 7386.

    Article  CAS  Google Scholar 

  11. Augeri, D. J.; Robl, J. A.; Betebenner, D. A.; Magnin, D. R.; Khanna, A.; Robertson, J. G.; Wang, A.; Simpkins, L. M.; Taunk, P.; Huang, Q.; Han, S.-P.; Abboa-Offei, B.; Cap, M.; Xin, L.; Tao, L.; Tozzo, E.; Welzel, G. E.; Egan, D. M.; Marcinkeviciene, J.; Chang, S. Y.; Biller, S. A.; Kirby, M. S.; Parker, R. A.; Hamann, L. G. J. Med. Chem. 2005, 48, 5025.

    Article  CAS  PubMed  Google Scholar 

  12. Fukatsu, K.; Uchikawa, O.; Kawada, M.; Yamano, T.; Yamashita, M.; Kato, K.; Hirai, K.; Hinuma, S.; Miyamoto, M.; Ohkawa, S. J. Med. Chem. 2002, 45, 4212.

    Article  CAS  PubMed  Google Scholar 

  13. Xia, J.; Yang, G.; Zhuge, R.; Liu, Y.; Zhang, W. Chem.–Eur. J. 2016, 22, 18354.

    Article  CAS  PubMed  Google Scholar 

  14. Goehring, R. R. Org. Prep. Proced. Int. 1994, 26, 476.

    Article  CAS  Google Scholar 

  15. Zhang, J.-S.; Chen, T.; Zhou, Y.; Yin, S.-F.; Han, L.-B. Org. Lett. 2018, 20, 6746.

    Article  CAS  PubMed  Google Scholar 

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The study was carried out with the support of the Russian Foundation for Basic Research within the framework of the scientific project No. 18-33-00075 mol_a.

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Authors and Affiliations

  1. D. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya Sq., Moscow, 125047, Russia

    Elvira R. Zaitseva

  2. Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow, 117997, Russia

    Alexander Yu. Smirnov, Nadezhda S. Baleeva & Mikhail S. Baranov

  3. Pirogov Russian National Research Medical University, 1 Ostrovitianov St., Moscow, 117997, Russia

    Mikhail S. Baranov

Authors
  1. Elvira R. Zaitseva
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  2. Alexander Yu. Smirnov
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  3. Nadezhda S. Baleeva
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  4. Mikhail S. Baranov
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Corresponding author

Correspondence to Alexander Yu. Smirnov.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(7), 676–678

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Zaitseva, E.R., Smirnov, A.Y., Baleeva, N.S. et al. Synthesis of spirocyclic pyrrolidines from cyclopentylideneacetic acid derivatives. Chem Heterocycl Comp 55, 676–678 (2019). https://doi.org/10.1007/s10593-019-02516-3

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  • DOI: https://doi.org/10.1007/s10593-019-02516-3

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