Research on Chemical Intermediates

, Volume 41, Issue 10, pp 7799–7813 | Cite as

One-pot Michael addition–oxidation reaction for the synthesis of coumarin–chromene hybrid compounds from 4-hydroxycoumarin and 3-nitro-2-phenyl-2H-chromene

  • Seetaram MohapatraEmail author
  • Sujitlal Bhakta
  • Subhendu Chakroborty
  • Manisha Tripathy
  • Sabita Nayak


An efficient and mild method for coumarin–chromene hybrid compounds involving Michael addition of 4-hydroxycoumarin with 3-nitro-2-phenyl-2H-chromene followed by aerial oxidation has been developed. Out of several bases screened for the above reaction, a few furnished the desired compounds in moderate-to good yields. Several hybrids of 4-hydroxycoumarin and 3-nitro-2-phenyl-2H-chromene were obtained following an easy-to-handle non-aqueous work-up procedure without chromatographic separation.

Graphical Abstract


4-Hydroxycoumarin Michael addition Nitro chromene Oxygen heterocyclic Oxidation 



Financial support from the DST to SN (fast track grant SR/FT/CS-139/2011) to SRM (fast Track grant SB/FT/CS-87/2012) and from the UGC to SN (major project 42-276/2013) are gratefully acknowledged. The authors acknowledge the National Institute of Science Education and Research, Bhubaneswar for NMR facility. Also the author thanks to Prof. A.C. Das (Retired Prof. Utkal University) for scientific discussion.

Supplementary material

11164_2014_1860_MOESM1_ESM.doc (10 mb)
Supplementary material 1 (DOC 10203 kb)


  1. 1.
    P. Perlmutter, Conjugate Addition Reactions in Organic Synthesis (Pergamon Press, Oxford, 1992)Google Scholar
  2. 2.
    C. Bhanja, S. Jena, S. Nayak, S. Mohapatra, Beilstein. J.O.C. 8, 1668 (2012)Google Scholar
  3. 3.
    R.-Q. Mei, X.-Y. Xu, L. Peng, F. Wang, F. Tian, L.-X. Wang, Org. Biomol. Chem. 11, 1286 (2013)CrossRefGoogle Scholar
  4. 4.
    M.R. Zanwar, M.J. Raihan, S.D. Gawande, V. Kavala, D. Janreddy, C.-W. Kuo, R. Ambre, C.-F. Yao, J. Org. Chem. 77, 6495 (2012)CrossRefGoogle Scholar
  5. 5.
    E. Ghabraie, M. Bararjanian, S. Balalaie, F. Rominger, H.R. Bijanzadeh, Helv. Chim. Acta 94, 1440 (2011)CrossRefGoogle Scholar
  6. 6.
    M. Zeeshan, V.O. Iaroshenko, S. Dudkin, D.M. Volochnyuk, P. Langner, Tetrahedron Let. 51, 3897 (2010)CrossRefGoogle Scholar
  7. 7.
    A.Z. Abyshev, V.A. Gindin, E.V. Semenov, E.M. Agaev, A.A. Abdulla-zade, A.B. Guseinov, Pharm. Chem. J. 40, 607 (2006)CrossRefGoogle Scholar
  8. 8.
    E. Adami, E. Marazzi-Uberti, C. Turba, Sci. Farmacol. 9, 61 (1959)Google Scholar
  9. 9.
    D. Chiarino, G.C Grancini, V. Frigeni, A. Carenzi, Eur. Pat. Appl. EP 284017 (1988)Google Scholar
  10. 10.
    A.C. Luchini, P. Rodrigues-Orsi, S.H. Cestari, L.N. Seito, A. Witaicenis, C.H. Pellizzon, L.C.D. Stasi, Biol. Pharm. Bull. 31, 1343 (2008)CrossRefGoogle Scholar
  11. 11.
    P. Stern, M. Dezelic, R. Kosak, Pathol. Pharmakol. 232, 356 (1957)CrossRefGoogle Scholar
  12. 12.
    Z.H. Chohan, A.U. Shaikh, A. Rauf, C.T. Supuran, J. Enz. Inhib. Med. Chem. 21, 741 (2006)CrossRefGoogle Scholar
  13. 13.
    M.A. Velasco-Velázquez, J. Agramonte-Hevia, D. Barrera, A. Jiménez-Orozco, M.J. García-Mondragón, N. Mendoza-Patiño, A. Landa, J. Mandoki, Cancer Lett. 198, 179 (2003)CrossRefGoogle Scholar
  14. 14.
    S.-Q. Yin, M. Shi, T.-T. Kong, C.-M. Zhang, K. Han, B. Cao, Z. Zhang, X. Du, L.-Q. Tang, X. Mao, Z.-P. Liu, Bioorg. Med. Chem. Lett. 23, 3314 (2013)CrossRefGoogle Scholar
  15. 15.
    J.J. Galano, M. Alias, R. Perez, A. Velazquez-Campoy, P.S. Hoffman, J. Sancho, J. Med. Chem. 56, 6248 (2013)CrossRefGoogle Scholar
  16. 16.
    B.C. Das, S. Mohapatra, P.D. Campbell, S. Nayak, S.M. Mahalingam, T. Evans, Tetrahedron Lett. 51, 2567 (2010)CrossRefGoogle Scholar
  17. 17.
    S. Mohapatra, S. Bhakta, N. Baral, S. Nayak, Res. Chem. Intermed (2014)Google Scholar
  18. 18.
    O.N. Chupakhin, V.N. Charushin, H.C. van der Plas, Nucleophilic Aromatic Substitution of Hydrogen (Academic Press, San Diego, 1994)Google Scholar

Copyright information

© Springer Science+Business Media Dordrecht 2014

Authors and Affiliations

  • Seetaram Mohapatra
    • 1
    Email author
  • Sujitlal Bhakta
    • 1
  • Subhendu Chakroborty
    • 1
  • Manisha Tripathy
    • 1
  • Sabita Nayak
    • 1
  1. 1.Organic Synthesis Laboratory, Lab No-180, Department of ChemistryRavenshaw UniversityCuttackIndia

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