Advertisement

Research on Chemical Intermediates

, Volume 41, Issue 6, pp 3759–3765 | Cite as

Synthesis of (aryl/heteroaryl)-(6-(aryl/heteroaryl)pyridin-3-yl)methanones

  • Dinesh Addla
  • Srinivas Kantevari
Article
  • 122 Downloads

Abstract

One-pot condensation of aryl/heteroaryl β-enaminones and ammonium acetate in the presence of CeCl3·7H2O–NaI led to the formation of novel (aryl/heteroaryl)(6-(aryl/heteroaryl)pyridin-3-yl)methanone in very good yields. Mechanistically, the reaction proceeds via tandem, regioselective Michael addition–cyclodehydration–elimination sequence.

Keywords

Condensation β-Enaminones Pyridine Cerium chloride Michael addition Cyclodehydration 

Notes

Acknowledgments

The authors are grateful to Dr. A. Kamal, Acting Director, IICT, and Dr. V. J. Rao, Head, CPC Division, IICT, Hyderabad, for their constant support, and encouragement, and for financial assistance from MLP & Network projects. D.A. is grateful to CSIR for a senior research fellowship.

Supplementary material

11164_2013_1487_MOESM1_ESM.docx (5.3 mb)
Supplementary material 1 (DOCX 5413 kb)

References

  1. 1.
    F. Monnier, M. Taillefer, Angew. Chem. Int. Ed. 48, 6954 (2009)CrossRefGoogle Scholar
  2. 2.
    F.H. John, Nature 455, 314 (2008)CrossRefGoogle Scholar
  3. 3.
    J. Bourgeois, I. Dion, P.H. Cebrowski, F. Loiseau, A.C. Bedard, A.M. Beauchemin, J. Am. Chem. Soc. 131, 874 (2009)CrossRefGoogle Scholar
  4. 4.
    B. Stanovnik, J. Svete, Chem. Rev. 104, 2433 (2004)CrossRefGoogle Scholar
  5. 5.
    A.A. Elassar, A.A. El-Khair, Tetrahedron. 59, 8463 (2003)CrossRefGoogle Scholar
  6. 6.
    S. Cacchi, G. Fabrizi, E. Filisti, Org. Lett. 10, 2629 (2008)CrossRefGoogle Scholar
  7. 7.
    P. Singh, P. Sharma, K. Bisetty, M.P. Mahajan, Tetrahedron 65, 8478 (2009)CrossRefGoogle Scholar
  8. 8.
    J. Bezenšek, T. Koleša, U. Grošelj, J. Wagger, K. Stare, A. Meden, J. Svete, B. Stanovnik, Tetrahedron 68, 516 (2012)CrossRefGoogle Scholar
  9. 9.
    S.M. Riyadh, Molecules. 16, 1834 (2011)CrossRefGoogle Scholar
  10. 10.
    F. Nasiri, M. Bayzidi, A. Zolali, Mol Divers 16, 619 (2012)CrossRefGoogle Scholar
  11. 11.
    S.M. Al-Mousawi, M.A. El-Apasery, M.H. Elnagdi, Molecules 15, 58 (2010)CrossRefGoogle Scholar
  12. 12.
    K. Srinivas, P. Santhosh Reddy, A. Dinesh, P. Siddamal Reddy, B. Sridhar, D. Sriram, P. Yogeeswari, ACS Comb. Sci. 13, 427 (2011)CrossRefGoogle Scholar
  13. 13.
    K. Srinivas, P. Santhosh Reddy, B. Sridhar, D. Sriram, P. Yogeeswari, Bioorg. Med. Chem. Lett. 21, 1214 (2011)CrossRefGoogle Scholar
  14. 14.
    K. Srinivas, A. Dinesh, B. Sridhar, Synthesis. 3745, 2010 (2010)Google Scholar
  15. 15.
    K. Srinivas, P. Siddamal Reddy, Synlett. 15, 2251 (2010)Google Scholar
  16. 16.
    B. Al-Saleh, M.M. Abdelkhalik, A.M. Eltoukhy, H.M. Elnagdi, J. Heterocycl. Chem. 39, 1035 (2002)CrossRefGoogle Scholar
  17. 17.
    A.M.M. Khalik, M.H. Elnagdi, Synth. Commun. 32, 159 (2002)CrossRefGoogle Scholar
  18. 18.
    K.M. Al-Zaydi, L.M. Nhari, R.M. Borik, M.H. Elnagdi, Green Chem. Lett. Rev. 3, 93 (2010)CrossRefGoogle Scholar
  19. 19.
    P.J. Tambade, Y.P. Patil, B.M. Bhanage, Curr. Org. Chem. 13, 1805 (2009)CrossRefGoogle Scholar
  20. 20.
    J. Comelles, A. Pericas, M. Moreno-Manas, A. Vallribera, ARKIVOC ix, 207 (2005)CrossRefGoogle Scholar
  21. 21.
    G. Bartoli, E. Marcantoni, L. Sambri, Synlett. 29, 2101 (2003)CrossRefGoogle Scholar
  22. 22.
    G. Bartoli, J.G. Fernanadez-Bolanos, G.D. Antonio, G. Foglia, S. Giuli, R. Gunnella, M. Mancinelli, E. Marcantoni, M. Paoletti, J. Org. Chem. 72, 6029 (2007)CrossRefGoogle Scholar
  23. 23.
    M. H. Khodaei, A. R. Khosropour, M. Kookhazadeh, Synlett. 1980 (2004)Google Scholar
  24. 24.
    J. Christofeers, T. Kauf, T. Werner, M. Rossle, Eur. J. Org. Chem. 2601 (2006)Google Scholar

Copyright information

© Springer Science+Business Media Dordrecht 2013

Authors and Affiliations

  1. 1.Crop Protection Chemicals Division, (Organic Chemistry Division-II)CSIR-Indian Institute of Chemical TechnologyHyderabadIndia

Personalised recommendations