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One-pot insertion of chalcones into the benzoylacetone backbone

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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.

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References

  1. C.F. Nising, S. Bräse, Chem. Soc. Rev. 41, 988–999 (2012)

    Article  CAS  Google Scholar 

  2. S.C. Jha, N.N. Joshi, Arkivoc vii, 167–196 (2002)

    Google Scholar 

  3. C. Bhanja, S. Jena, S. Nayak, S. Mohapatra, S. Beilstein, J. Org. Chem. 8, 1668–1694 (2012)

    CAS  Google Scholar 

  4. B.D. Mather, K. Viswanathan, K.M. Miller, T.E. Long, Prog. Polym. Sci. 31, 487–531 (2006)

    Article  CAS  Google Scholar 

  5. A.Y. Barkov, V.Y. Korotaev, V.Y. Sosnovskikh, Tetrahedron Lett. 54, 6819–6821 (2013)

    Article  CAS  Google Scholar 

  6. J. Wang, H. Li, L. Zu, W. Jiang, H. Xie, W. Duan, W. Wang, J. Am. Chem. Soc. 128, 12652–12653 (2006)

    Article  CAS  Google Scholar 

  7. H. Naka, N. Kanase, M. Ueno, Y. Kondo, Chem. Eur. J. 14, 5267–5274 (2008)

    Article  CAS  Google Scholar 

  8. X. Li, L. Cun, C. Lian, L. Zhong, Y. Chen, J. Liao, J. Zhu, J. Deng, Org. Biomol. Chem. 6, 349–353 (2008)

    Article  CAS  Google Scholar 

  9. J. Shi, M. Wang, L. He, K. Zheng, X. Liu, L. Lin, X. Feng, Chem. Commun. 31, 4711–4713 (2009)

    Article  CAS  Google Scholar 

  10. Z. Nowakowska, Eur. J. Med. Chem. 42, 125–137 (2007)

    Article  CAS  Google Scholar 

  11. S.N.A. Bukhari, M. Jasamai, I. Jantan, W. Ahmad, Mini-Rev. Org. Chem. 10, 73–83 (2013)

    Article  CAS  Google Scholar 

  12. S. Singh, P.K. Sharma, N. Kumar, R. Dudhe, Asian. J. Pharm. Biol. Res. 1, 412–418 (2011)

    Google Scholar 

  13. Y. Song, H. Jing, B. Li, D. Bai, Chem. Eur. J. 17, 8731–8738 (2011)

    Article  CAS  Google Scholar 

  14. H.S.P. Rao, S. Jothilingam, J. Chem. Sci. 117, 323–328 (2005)

    Article  CAS  Google Scholar 

  15. Y.-M. Ren, C. Cai, J. Chem. Res. 35, 176–178 (2011)

    Article  CAS  Google Scholar 

  16. S. Senguttuvan, S. Nagarajan, J. Heterocycl. Chem. 46, 1346–1348 (2009)

    Article  CAS  Google Scholar 

  17. N.A. Al-Jaber, A.S.A. Bougasim, M.M.S. Karah, J. Saudi Chem. Soc. 16, 45–53 (2012)

    Article  CAS  Google Scholar 

  18. M. Mečiarová, Š. Toma, Chem. Eur. J. 13, 1268–1272 (2007)

    Article  CAS  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  20. SHELXTL Reference Manual, Version 5.1, Bruker AXS, Analytic X-ray Systems, Inc., Madison, WI, (1997)

  21. SMART & SAINT Software Reference Manuals, Version 6.22, Bruker AXS Analytic X-ray Systems, Inc., Madison, WI, (2000)

  22. G.M. Sheldrick, SADABS Software for Empirical Absorption Correction (University of Göttingen, Göttingen, 2000)

    Google Scholar 

  23. C. Hansch, A. Leo, W.R. Taft, Chem. Rev. 91, 165–195 (1991)

    Article  CAS  Google Scholar 

  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)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work has been partially supported by the Baku State University, Azerbaijan.

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Authors and Affiliations

  1. Department of Chemistry, Baku State University, Z. Xalilov Str. 23, 1148, Baku, Azerbaijan

    Farid N. Naghiyev, Atash V. Gurbanov, Abel M. Maharramov, Ibrahim G. Mamedov, Mirze A. Allahverdiyev & Kamran T. Mahmudov

  2. Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, 1049–001, Lisbon, Portugal

    Kamran T. Mahmudov

Authors
  1. Farid N. Naghiyev
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  2. Atash V. Gurbanov
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  3. Abel M. Maharramov
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  4. Ibrahim G. Mamedov
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  5. Mirze A. Allahverdiyev
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  6. Kamran T. Mahmudov
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Corresponding author

Correspondence to Kamran T. Mahmudov.

Electronic supplementary material

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13738_2015_705_MOESM1_ESM.doc

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

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Naghiyev, F.N., Gurbanov, A.V., Maharramov, A.M. et al. One-pot insertion of chalcones into the benzoylacetone backbone. J IRAN CHEM SOC 13, 1–6 (2016). https://doi.org/10.1007/s13738-015-0705-x

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  • DOI: https://doi.org/10.1007/s13738-015-0705-x

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