Skip to main content
Log in

One-pot of three-component synthesis of novel amino-spiroindene derivatives

  • Original Paper
  • Published:
Journal of the Iranian Chemical Society Aims and scope Submit manuscript

Abstract

A facile and efficient one-pot three-component synthesis of the amino-spiroindene derivatives was achieved, via the reaction of ninhydrin, malononitrile or ethylcyanoacetate and various reagents including 1, 2- and 1,3-dicarbonyl compounds/enols.

Graphical Abstract

.

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.

Scheme 1
Scheme 2
Scheme 3
Scheme 4
Scheme 5

Similar content being viewed by others

References

  1. R.V.A. Orru, M. de Greef, Synthesis 1471 (2003)

  2. G. Balme, E. Bossharth, N. Monteiro, Eur. J. Org. Chem. 4101 (2003)

  3. S. Brase, C. Gil, K. Knepper, Bioorg. Med. Chem. 10, 2415 (2002)

    Article  CAS  Google Scholar 

  4. A. Domling, I. Ugi, Angew. Chem. Int. Ed. 39, 3168 (2000)

    Article  CAS  Google Scholar 

  5. L. Weber, Drug Discov. Today 7, 143 (2002)

    Article  CAS  Google Scholar 

  6. A. Domling, Curr. Opin. Chem. Biol. 6, 306 (2002)

    Article  CAS  Google Scholar 

  7. A. Nefzi, J.M. Ostresh, R.A. Houghten, Chem. Rev. 97, 449 (1997)

    Article  CAS  Google Scholar 

  8. L.A. Thompson, Curr. Opin. Chem. Biol. 4, 324 (2000)

    Article  CAS  Google Scholar 

  9. A.A. Hassan, K.M. El-Shaieb, D. Dopp, ARKIVOC 139 (2005)

  10. A. Yenesew, J.O. Midiwo, P.G. Waterman, J. Nat. Proud. 60, 806 (1997)

    Article  CAS  Google Scholar 

  11. Z. Latif, T.G. Hartley, M.J. Rice, R.D. Waigh, P.G. Waterman, J. Nat. Proud. 61, 614 (1998)

    Article  CAS  Google Scholar 

  12. R. Pradhan, M. Patra, A.K. Behera, B.K. Mishra, R.K. Behera, Tetrahedron. 62, 779 (2006)

    Article  CAS  Google Scholar 

  13. R.C. Gadwood, B.V. Kamdar, L.A.C. Dubray, M.L. Wolfe, M.P. Smith, W. Watt, S.A. Mizsak, V.E. Groppit, J. Med. Chem. 36, 1480 (1993)

    Article  CAS  Google Scholar 

  14. B.L. Bourdonnec, R.T. Windh, L.K. Leister, Q.J. Zhou, C.W. Ajello, M. Gu, G. Chu, P.A. Tuthill, W.M. Barker, M. Koblish, D.D. Wiant, T.M. Graczyk, S. Belanger, J.A. Cassel, M.S. Feschenko, B.L. Brogdon, S.A. Smith, M.J. Der-elanko, J. Med. Chem. 52, 5685 (2009)

    Article  CAS  Google Scholar 

  15. M. Sannigrahi, Tetrahedron 55, 9007 (1999)

    Article  CAS  Google Scholar 

  16. D.M. James, H.B. Kunze, D.J. Faulkner, J. Nat. Prod. 54, 1137 (1991)

    Article  CAS  Google Scholar 

  17. J. Kobayashi, M. Tsuda, K. Agemi, H. Shigemiri, M. Ishibashi, T. Sasaki, Y. Mikami, Tetrahedron 47, 6617 (1991)

    Article  CAS  Google Scholar 

  18. N. Srivastav, A. Mittal, A. Kumar, J. Chem. Soc. Chem. Commun. 493 (1992)

  19. A.T. Khan, T. Parvin, L.H. Choudhury, J. Org. Chem. 73, 8398 (2008)

    Article  CAS  Google Scholar 

  20. C. Simon, T. Constantieux, J. Rodriguez, Eur. J. Org. Chem. 4957 (2004)

  21. J. Sun, E.Y. Xia, L.L. Zhang, C.G. Yan, Eur. J. Org. Chem. 5247 (2009)

  22. M.R. Nabid, S.J.T. Rezaei, R. Ghahremanzadeh, A. Bazgir, Ultrason. Sonochem. 17, 159 (2010)

    Article  CAS  Google Scholar 

  23. J. M. Khurana, S. Yadav, Aust. J. Chem. 65(3), 314 (2012)

    Google Scholar 

Download references

Acknowledgments

We gratefully acknowledge, the Vali-e-Asr University of Rafsanjan Faculty Research Grant for financial support.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Ali Darehkordi.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 16506 kb)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Darehkordi, A., Karimi-Taleghani, Z. & Pouralimardan, O.A. One-pot of three-component synthesis of novel amino-spiroindene derivatives. J IRAN CHEM SOC 11, 623–629 (2014). https://doi.org/10.1007/s13738-013-0332-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-013-0332-3

Keywords

Navigation