Skip to main content

Advertisement

SpringerLink
Log in

The legend of 4-aminocoumarin: use of the Delépine reaction for synthesis of 4-iminocoumarin

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

Abstract

Use of the Delépine reaction for synthesis of 4-aminocoumarin from 4-chlorocoumarin was not successful. The product was 4-iminocoumarin instead of 4-aminocoumarin. The 4-iminocoumarin was characterized by elemental analysis and spectral studies (FT-IR, 1H NMR, 13C NMR). Density functional theory calculations for 4-iminocoumarin were performed using molecular structure with optimized geometry. Molecular orbital calculations provided a detailed description of the orbitals, including spatial characteristics, nodal patterns, and the contributions of individual atoms.

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

Scheme 1
Scheme 2
Fig. 1
Fig. 2

Similar content being viewed by others

References

  1. A.A. Al-Amiery, A.A. Mohammed, H. Ibrahim, World Acad. Sci. Eng. Technol. 57, 433 (2009)

    Google Scholar 

  2. A.A. Al-Amiery, Y. Al-Majedy, H. Abdulreazak, H. Abood, Bioinorg. Chem. Appl. 2011, 1–6 (2011)

    Article  Google Scholar 

  3. A.A. Al-Amiery, Y. Al-Majedy, H. Ibrahim, A. Temimi, Org. Med. Chem. Lett. 2, 1–7 (2012)

    Article  Google Scholar 

  4. A.A. Al-Amiery, A. Kadhum, A. Mohamad, Bioinorg. Chem. Appl. 2012, 1–5 (2012)

    Article  Google Scholar 

  5. A.A. Al-Amiery, A.A. Mohammed, G.M. Alhyali, J. Appl. Sci. Res. 7(4), 470 (2011)

    Google Scholar 

  6. A.A. Al-Amiery, Res. Chem. Intermed. 38, 745–759 (2012)

    Article  CAS  Google Scholar 

  7. A. El-Agrody, M. Abd El-Latif, N. El-Hady, A. Fakery, A. Bedair, Molecules 6, 519 (2001)

    Article  CAS  Google Scholar 

  8. S. Kovalenko, I. Bylov, K. Sytnik, V. Chernykh, Y. Bilokin, Molecules 5, 1146 (2000)

    Article  CAS  Google Scholar 

  9. S. Parmer, R. Kumar, J. Med. Chem. 11, 635 (1968)

    Article  Google Scholar 

  10. Y.D. Reddy, V.V. Somayajulu, J. Indian Chem. Soc. 58, 599 (1981)

    CAS  Google Scholar 

  11. T.O. Soine, J. Pharm. Sci. 53, 231 (1964)

    Article  CAS  Google Scholar 

  12. M.M. Dutta, B.N. Goswani, J.C.S. Kataky, J. Heterocycl. Chem. 23, 793 (1986)

    Article  CAS  Google Scholar 

  13. A.A. Al-Amiery, A. Musa, A. Kadhum, A. Mohamad, Molecules 16, 6833 (2011)

    Article  CAS  Google Scholar 

  14. A.A. Al-Amiery, A. Kadhum, A. Mohamad, Molecules 17, 5713 (2012)

    Article  CAS  Google Scholar 

  15. A. Kadhum, A.A. Al-Amiery, A. Musa, A. Mohamad, Int. J. Mol. Sci. 12, 5747 (2011)

    Article  CAS  Google Scholar 

  16. A. Kadhum, A. Mohamad, A.A. Al-Amiery, M. Takriff, Molecules 16, 6969 (2011)

    Article  CAS  Google Scholar 

  17. A.A. Al-Amiery, R. Al-Bayati, K. Saour, M. Radi, Res. Chem. Intermed. 38, 559 (2012)

    Article  CAS  Google Scholar 

  18. V. Kelly, E. Ellis, M. Manson, Cancer Res. 60, 957 (2000)

    CAS  Google Scholar 

  19. S. Kirkiacharian, D. Thuy, S. Sicsic, R. Bakhchinian, R. Kurkjian, T. Tonnaire, Farmaco 57, 703 (2002)

    Article  CAS  Google Scholar 

  20. D. Suzuki, M. Yu, L. Xie, S. Morris, K. Lee, Med. Res. Rev. 23, 322 (2003)

    Article  Google Scholar 

  21. V. Zagorevskii, N. Dudykina, Zh. Obsch. Khim. 32, 2384 (1962)

    CAS  Google Scholar 

  22. I. Manolov, N. Danchev, Eur. J. Med. Chem. Chim. Ther. 30, 531 (1995)

    Article  CAS  Google Scholar 

  23. H. Uno, M. Kurokawa, H. Nishimura, Chem. Pharm. Bull. 24, 644 (1976)

    Article  CAS  Google Scholar 

  24. I. Ivanov, S. Karagiosov, I. Manolov, Arch. Pharm. (Weinh.) 61, 324 (1991)

    Google Scholar 

  25. A.P. Chavan, J. Chem. Res. 3, 179 (2006)

    Google Scholar 

  26. B. Stamboliyska, V. Janevska, B. Shivachev, P. Nikolova, G. Stojkovic, B. Mikhova, E. Popovski, Arkivoc X, 62 (2010)

    Google Scholar 

  27. M. Delépine, Bull. Soc. Chim. Fr. 13, S. 352–361 (1895)

    Google Scholar 

  28. R. Alexander, Name Reactions in Organic Chemistry, 2nd edn. (Academic Press, New York, 1961)

    Google Scholar 

  29. D.P. Spalding, H.S. Mosher, F.C. Whitmore, J. Am. Chem. Soc. 72, 5338 (1950)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors gratefully acknowledge Universiti Kebangsaan Malaysia for support of this project.

Author information

Authors and Affiliations

  1. Department of Chemical and Processing Engineering, Faculty of Engineering and Built Environment, Universiti Kebangsaan Malaysia, 43600, Bangi, Selangor, Malaysia

    Ahmed A. Al-Amiery, Abdul Amir H. Kadhum & Abu Bakar Mohamad

  2. Biotechnology Division, Applied Science Department, University of Technology, Baghdad, 10066, Iraq

    Ahmed A. Al-Amiery, Y. K. Al-Majedy, Hiba H. Ibraheem, Ali A. Al-Temimi & Redah I. Al-Bayati

Authors
  1. Ahmed A. Al-Amiery
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Abdul Amir H. Kadhum
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Y. K. Al-Majedy
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Hiba H. Ibraheem
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Ali A. Al-Temimi
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Redah I. Al-Bayati
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Abu Bakar Mohamad
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ahmed A. Al-Amiery.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Al-Amiery, A.A., Kadhum, A.A.H., Al-Majedy, Y.K. et al. The legend of 4-aminocoumarin: use of the Delépine reaction for synthesis of 4-iminocoumarin. Res Chem Intermed 39, 1385–1391 (2013). https://doi.org/10.1007/s11164-012-0694-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-012-0694-7

Keywords

Search

Navigation