Skip to main content
Log in

Synthesis of the complex bridged 1,5-oxazabicycles via one-pot reactions of 4,5-diazafluoren-9-one, alkyl halides, and cyclic 1,3-diketone

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

An efficient and practical procedure for the preparation of the complex bridged 1,5-oxazabicycles was developed via a one-pot domino reaction of 4,5-diazafluoren-9-one, reactive alkyl halides, and cyclic 1,3-dicarbonyl compounds.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2

Similar content being viewed by others

References

  1. L. A. Thompson and J. A. Ellman, Chem. Rev., 96, 555 (1996).

    Article  CAS  Google Scholar 

  2. D. L. Klayman, J. P. Scovill, J. F. Bartosevich, and C. J. Mason, J. Med. Chem., 22, 1367 (1979).

    Article  CAS  Google Scholar 

  3. E. Vedejs, R. J. Galante, and P. G. Goekjian, J. Am. Chem. Soc., 120 , 3613 (1998).

    Article  CAS  Google Scholar 

  4. D. C. Palmer and M. J. Strauss, Chem. Rev., 77, 1 (1977).

    Article  CAS  Google Scholar 

  5. A. Deiters and S. F. Martin, Chem. Rev., 104, 2199 (2004).

    Article  CAS  Google Scholar 

  6. P. A. Evans and B. Holmes, Tetrahedron, 47, 9131 (1991).

    Article  CAS  Google Scholar 

  7. D. Staerk, M. Witt, H. A. Oketch-Rabah, and J. W. Jaroszewski, Org. Lett., 5, 2793 (2003).

    Article  Google Scholar 

  8. G. Broggini, L. Bruch, L. Garanti, and G. Zecchi, J. Chem. Soc., Perkin Trans. 1, 433 (1994).

  9. W. A. L. Van Otterlo, G. L. Morgans, S. D. Khanye, B. A. Aderibigbe, J. P. Michael, and D. G. Billing, Tetrahedron Lett., 45, 9171 (2004).

    Article  Google Scholar 

  10. A. Klapars, S. Parris, K. W. Anderson, and S. L. Buchwald, J. Am. Chem. Soc., 126, 3529 (2004).

    Article  CAS  Google Scholar 

  11. T. Yang, C. Lin, H. Fu, Y. Jiang, and Y. Zhao, Org. Lett., 7, 4781 (2005).

    Article  CAS  Google Scholar 

  12. K. Mizuno, M. Sawa, H. Harada, I. Taoka, H. Yamashita, M. Oue, H. Tsujiuchi, Y. Arai, S. Suzuki, Y. Furutani, and S. Kato, Bioorg. Med. Chem., 13, 855 (2005).

    Article  CAS  Google Scholar 

  13. J. K. Mishra, K. Samanta, M. Jain, M. Dikshit, and G. Panda, Bioorg. Med. Chem. Lett., 20, 244 (2010).

    Article  CAS  Google Scholar 

  14. T. Ventrice, E. M. Campi, W. R. Jackson, and A. F. Patti, Tetrahedron, 57, 7557 (2001).

    Article  CAS  Google Scholar 

  15. J. Agejas, F. Delgado, J. J. Vaquero, J. L. García-Navío, and C. Lamas, Tetrahedron Lett., 43, 8025 (2002).

    Article  CAS  Google Scholar 

  16. A. Neogi, T. P. Majhi, R. Mukhopadhyay, and P. Chattopadhyay, J. Org. Chem., 71, 3291 (2006).

    Article  CAS  Google Scholar 

  17. J. Rujirawanich and T. Gallagher, Org. Lett., 11, 5494 (2009).

    Article  CAS  Google Scholar 

  18. E. Ullah, S. Rotzoll, A. Schmidt, D. Michalikc, and P. Langer, Tetrahedron Lett., 46, 8997 (2005).

    Article  CAS  Google Scholar 

  19. F. M. Moghaddam, Z. Mirjafary, H. Saeidian, S. Taheri, M. Doulabi, and M. Kiamehr, Tetrahedron, 66, 134 (2010).

    Article  CAS  Google Scholar 

  20. F. M. Moghaddam, S. Taheri, Z. Mirjafary, and H. Saeidian, Synlett, 123 (2010).

  21. J. F. Wang, Y. X. Liao, P. Y. Kuo, Y. H. Gau, and D. H. Yang, Synlett, 2791 (2006).

  22. J. T. Lai, P. Y. Kuo, Y. H. Gau, and D. Y. Yang, Tetrahedron Lett., 48, 7796 (2007).

    Article  CAS  Google Scholar 

  23. D. H. Yang, Y. S. Chen, P. Y. Kuo, J. T. Lai, C. M. Jiang, C. H. Lai, Y. H. Liao, and P. T. Chou, Org. Lett., 9, 5287 (2007).

    Article  CAS  Google Scholar 

  24. C. H. Lin, J. L. Chen, and D. H. Yang, J. Comb. Chem., 12, 119 (2010).

    Article  CAS  Google Scholar 

  25. F. M. Moghaddam, M. Mirjafary, H. Saeidian, S. Taheria, and B. Soltanzadeh, Tetrahedron, 66, 3678 (2010).

    Article  CAS  Google Scholar 

  26. F. M. Moghaddam, Z. Mirjafary, H. Saeidian, S. Taheri, and M. R. Khodabakhshi, Tetrahedron Lett., 51, 2704 (2010).

    Article  CAS  Google Scholar 

  27. F. M. Moghaddam, S. Taheria, Z. Mirjafarya, H. Saeidianb, M. Kiamehra, and M. Tafazzolia, Helv. Chim. Acta, 92, 142 (2011).

    Article  Google Scholar 

  28. L. Hui and C. G. Yan, Tetrahedron, 67, 2863 (2011).

    Article  Google Scholar 

  29. J. E. Dickeson and L. A. Summers, Aust. J. Chem., 23, 1023 (1970).

    Article  CAS  Google Scholar 

  30. A. V. Rotaru, R. P. Danac, and I. D. Druta, J. Heterocycl. Chem., 41, 983 (2004).

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to C. G. Yan.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 706-714, April, 2012.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Hui, L., Gao, S. & Yan, C.G. Synthesis of the complex bridged 1,5-oxazabicycles via one-pot reactions of 4,5-diazafluoren-9-one, alkyl halides, and cyclic 1,3-diketone. Chem Heterocycl Comp 48, 658–665 (2012). https://doi.org/10.1007/s10593-012-1040-0

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-012-1040-0

Keywords

Navigation