Journal of the Iranian Chemical Society

, Volume 13, Issue 1, pp 1–6 | Cite as

One-pot insertion of chalcones into the benzoylacetone backbone

  • Farid N. Naghiyev
  • Atash V. Gurbanov
  • Abel M. Maharramov
  • Ibrahim G. Mamedov
  • Mirze A. Allahverdiyev
  • Kamran T. Mahmudov
Original Paper

Abstract

Interaction of 1-phenylbutane-1,3-dione and chalcones in the presence of a base gives, in one step, good to high yields cyclic and unusual acyclic insertion products in ratios which depend on substrate, catalyst, and reaction conditions. All the synthesized compounds are characterized using IR, 1H and 13C NMR spectroscopies, ESI–MS, and single-crystal X-ray diffraction (for one compound) analysis.

Keywords

Michael addition Chalcone Benzoylacetone Active methylene compounds 

Supplementary material

13738_2015_705_MOESM1_ESM.doc (4.6 mb)
Supplementary material 1 (DOC 4736 kb) Supplementary data (copies of 1H and 13C NMR spectra for all compounds) associated with this article can be found, in the online version, at http://dx.doi.org/10

References

  1. 1.
    C.F. Nising, S. Bräse, Chem. Soc. Rev. 41, 988–999 (2012)CrossRefGoogle Scholar
  2. 2.
    S.C. Jha, N.N. Joshi, Arkivoc vii, 167–196 (2002)Google Scholar
  3. 3.
    C. Bhanja, S. Jena, S. Nayak, S. Mohapatra, S. Beilstein, J. Org. Chem. 8, 1668–1694 (2012)Google Scholar
  4. 4.
    B.D. Mather, K. Viswanathan, K.M. Miller, T.E. Long, Prog. Polym. Sci. 31, 487–531 (2006)CrossRefGoogle Scholar
  5. 5.
    A.Y. Barkov, V.Y. Korotaev, V.Y. Sosnovskikh, Tetrahedron Lett. 54, 6819–6821 (2013)CrossRefGoogle Scholar
  6. 6.
    J. Wang, H. Li, L. Zu, W. Jiang, H. Xie, W. Duan, W. Wang, J. Am. Chem. Soc. 128, 12652–12653 (2006)CrossRefGoogle Scholar
  7. 7.
    H. Naka, N. Kanase, M. Ueno, Y. Kondo, Chem. Eur. J. 14, 5267–5274 (2008)CrossRefGoogle Scholar
  8. 8.
    X. Li, L. Cun, C. Lian, L. Zhong, Y. Chen, J. Liao, J. Zhu, J. Deng, Org. Biomol. Chem. 6, 349–353 (2008)CrossRefGoogle Scholar
  9. 9.
    J. Shi, M. Wang, L. He, K. Zheng, X. Liu, L. Lin, X. Feng, Chem. Commun. 31, 4711–4713 (2009)CrossRefGoogle Scholar
  10. 10.
    Z. Nowakowska, Eur. J. Med. Chem. 42, 125–137 (2007)CrossRefGoogle Scholar
  11. 11.
    S.N.A. Bukhari, M. Jasamai, I. Jantan, W. Ahmad, Mini-Rev. Org. Chem. 10, 73–83 (2013)CrossRefGoogle Scholar
  12. 12.
    S. Singh, P.K. Sharma, N. Kumar, R. Dudhe, Asian. J. Pharm. Biol. Res. 1, 412–418 (2011)Google Scholar
  13. 13.
    Y. Song, H. Jing, B. Li, D. Bai, Chem. Eur. J. 17, 8731–8738 (2011)CrossRefGoogle Scholar
  14. 14.
    H.S.P. Rao, S. Jothilingam, J. Chem. Sci. 117, 323–328 (2005)CrossRefGoogle Scholar
  15. 15.
    Y.-M. Ren, C. Cai, J. Chem. Res. 35, 176–178 (2011)CrossRefGoogle Scholar
  16. 16.
    S. Senguttuvan, S. Nagarajan, J. Heterocycl. Chem. 46, 1346–1348 (2009)CrossRefGoogle Scholar
  17. 17.
    N.A. Al-Jaber, A.S.A. Bougasim, M.M.S. Karah, J. Saudi Chem. Soc. 16, 45–53 (2012)CrossRefGoogle Scholar
  18. 18.
    M. Mečiarová, Š. Toma, Chem. Eur. J. 13, 1268–1272 (2007)CrossRefGoogle Scholar
  19. 19.
    H.-M. Yang, Y.-H. Gao, L. Li, Z.-Y. Jiang, G.-Q. Lai, C.-G. Xia, L.-W. Xu, Tetrahedron Lett. 51, 3836–3839 (2010)CrossRefGoogle Scholar
  20. 20.
    SHELXTL Reference Manual, Version 5.1, Bruker AXS, Analytic X-ray Systems, Inc., Madison, WI, (1997)Google Scholar
  21. 21.
    SMART & SAINT Software Reference Manuals, Version 6.22, Bruker AXS Analytic X-ray Systems, Inc., Madison, WI, (2000)Google Scholar
  22. 22.
    G.M. Sheldrick, SADABS Software for Empirical Absorption Correction (University of Göttingen, Göttingen, 2000)Google Scholar
  23. 23.
    C. Hansch, A. Leo, W.R. Taft, Chem. Rev. 91, 165–195 (1991)CrossRefGoogle Scholar
  24. 24.
    K.T. Mahmudov, M.N. Kopylovich, A.M. Maharramov, M.M. Kurbanova, A.V. Gurbanov, A.J.L. Pombeiro, Coord. Chem. Rev. 265, 1–37 (2014)CrossRefGoogle Scholar

Copyright information

© Iranian Chemical Society 2015

Authors and Affiliations

  • Farid N. Naghiyev
    • 1
  • Atash V. Gurbanov
    • 1
  • Abel M. Maharramov
    • 1
  • Ibrahim G. Mamedov
    • 1
  • Mirze A. Allahverdiyev
    • 1
  • Kamran T. Mahmudov
    • 1
    • 2
  1. 1.Department of ChemistryBaku State UniversityBakuAzerbaijan
  2. 2.Centro de Química Estrutural, Instituto Superior TécnicoUniversidade de LisboaLisbonPortugal

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