Skip to main content
SpringerLink
Log in

Efficient synthesis of novel benzo [f]imidazo[1,2-d][1,4]oxazepine-5(6H)-one derivatives

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

A convenient and efficient method is described for the synthesis of novel tricyclic scaffolds incorporating an imidazole ring and medium-sized benzoxazepine ring, via the reaction of 1,2-diketons, 2-formyl phenoxy acetic acids and ammonium acetate in acetic acid under reflux conditions, and then the addition of thionyl chloride to produce lactam in the absence of a catalyst.

Graphical Abstract

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Scheme 1
Scheme 2

Similar content being viewed by others

References

  1. G.L. Grunewald, V.H. Dahanukar, P. Ching, K.R. Crisclone, J. Med. Chem. 39, 3539 (1996)

    Article  CAS  Google Scholar 

  2. G. Steiner, A. Franke, E. Hädicke, D. Lenke, H.J. Teschendorf, H.P. Hofmann, H. Kreiskott, W.J. Worstmann, J. Med. Chem. 29, 1877 (1986)

    Article  CAS  Google Scholar 

  3. I.A. O’Neil, C.L. Murray, R.C. Hunter, S.B. Kalindjian, T.C. Jenkins, Synlett 1, 75 (1997)

    Article  Google Scholar 

  4. Y. Liao, B.J. Venhuis, N. Rodenhuis, W. Timmerman, H. Wikström, E. Meier, G.D. Bartoszyk, H. Böttcher, C.A. Seyfried, S. Sundell, J. Med. Chem. 42, 2235 (1999)

    Article  CAS  Google Scholar 

  5. F. Novelli, T. Bruno, F. Sparatore, IL Farmaco 52, 499 (1997)

    CAS  Google Scholar 

  6. G.N. Walker, R.T. Smith, J. Org. Chem. 36, 305 (1997)

    Article  Google Scholar 

  7. K. Goutham, D.A. Kumar, S. Suresh, B. Sridhar, R. Narender, G.V. Karunakar, J. Org. Chem. 80, 11162 (2015)

    Article  CAS  Google Scholar 

  8. L.M. Greene, G. Campiani, M. Lawler, D.C. Williams, D.M. Zisterer, Mol. Pharmacol. 73, 419 (2008)

    Article  CAS  Google Scholar 

  9. A.M. McElligott, E.N. Maginn, L.M. Greene, S. McGuckin, A. Hayat, P.V. Browne, S. Butini, G. Campiani, M.A. Catherwood, E. Vandenberghe, D.C. Williams, D.M. Zisterer, M. Lawler, Cancer Res. 69, 8366 (2009)

    Article  CAS  Google Scholar 

  10. M.E. Derieg, L.H. Sternbach, J. Heterocycl. Chem. 3, 237 (1996)

    Article  Google Scholar 

  11. J. Pecher, A. Waefelaer, Bull. Soc. Chim. Belg. 87, 911 (1978)

    Article  CAS  Google Scholar 

  12. H. Heaney, K.F. Shuhaibar, Tetrahedron Lett. 35, 2751 (1994)

    Article  CAS  Google Scholar 

  13. M.T. ElGihani, H. Heaney, K.F. Shuhaibar, Synlett 9, 871 (1996)

    Article  Google Scholar 

  14. K.R. Levan, C.A. Root, Inorg. Chem. 20, 3566 (1981)

    Article  CAS  Google Scholar 

  15. K.R. Levan, C.A. Root, J. Org. Chem. 46, 2404 (1981)

    Article  CAS  Google Scholar 

  16. M. Mahdavi, N. Foroughi, M. Saeedi, M. Karimi, H. Alinezhad, A. Foroumadi, A. Shafiee, T. Akbarzadeh, Synlett 25, 385 (2014)

    CAS  Google Scholar 

  17. M. Mahdavi, R. Hariri, M. Saeedi, M. Karimi, H. Alinezhad, A. Foroumadi, A. Shafiee, T. Akbarzadeh, Tetrahedron Lett. 56, 7082 (2015)

    Article  CAS  Google Scholar 

  18. S. Farzipour, M. Saeedi, M. Mahdavi, H. Yavari, M. Mirzahekmati, N. Ghaemi, A. Foroumadi, A. Shafiee, Synth. Commun. 44, 481 (2013)

    Article  Google Scholar 

  19. H. Alinezhad, M. Tajbakhsh, M. Zare, J. Fluor. Chem. 132, 995 (2011)

    Article  CAS  Google Scholar 

  20. M. Weiss, J. Am. Chem. Soc. 74, 200 (1952)

    Article  CAS  Google Scholar 

  21. H. Alinezhad, S.M. Tavakkoli, S. Res. Chem. Intermed. 41, 5931 (2015)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This research was supported by grants from the University of Mazandaran and the research council of Tehran University of Medical Sciences.

Author information

Authors and Affiliations

  1. Faculty of Chemistry, University of Mazandaran, Babolsr, Iran

    Hossein Yavari, Heshmatoallah Alinezhad & Mahmood Tajbakhsh

Authors
  1. Hossein Yavari
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Heshmatoallah Alinezhad
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Mahmood Tajbakhsh
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Heshmatoallah Alinezhad.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 6595 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Yavari, H., Alinezhad, H. & Tajbakhsh, M. Efficient synthesis of novel benzo [f]imidazo[1,2-d][1,4]oxazepine-5(6H)-one derivatives. Res Chem Intermed 43, 3283–3290 (2017). https://doi.org/10.1007/s11164-016-2825-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-016-2825-z

Keywords

Search

Navigation