Skip to main content
Log in

An environmentally benign protocol: catalyst-free Michael addition of aromatic amines to α,β-unsaturated ketones in glycerol

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

Glycerol was used as a reaction medium as well as promoter for aza-Michael addition of aromatic amines to electronic deficient α,β-unsaturated ketones. Various aromatic amines can react smoothly with chalcone, 2-cyclohexen-1-one, 2-cyclopenten-1-one, and ethyl vinyl ketone to achieve good to excellent yields in the absence of any catalyst.

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.

Similar content being viewed by others

References

  1. A. Corma, S. Iborra, A. Velty, Chem. Rev. 107, 2411 (2007)

    Article  CAS  Google Scholar 

  2. N. Armaroli, V. Balzani, Angew. Chem. Int. Ed. 46, 52 (2007)

    Article  CAS  Google Scholar 

  3. A. Wolfson, C. Dlugy, Y. Shotland, Environ. Chem. Lett. 5, 67 (2007)

    Article  CAS  Google Scholar 

  4. A. Wolfson, C. Dlugy, Chem. Pap. 61, 228 (2007)

    Article  CAS  Google Scholar 

  5. A. Karam, N. Villandier, M. Delample, C.K. Koerkamp, J.-P. Douliez, R. Granet, P. Krausz, J. Barrault, F. Jérôme, Chem. Eur. J. 14, 10196 (2008)

    Article  CAS  Google Scholar 

  6. F. He, P. Li, Y.-L. Gu, G.-X. Li, Green Chem. 11, 1767 (2009)

    Article  CAS  Google Scholar 

  7. Y.-F. Wang, T. Izawa, S. Kobayashi, M. Ohno, J. Am. Chem. Soc. 104, 6465 (1982)

    Article  CAS  Google Scholar 

  8. Y. Hayashi, J.J. Rode, E.J. Corey, J. Am. Chem. Soc. 118, 5502 (1996)

    Article  CAS  Google Scholar 

  9. S. Fustero, B. Pina, E. Salavert, A. Navarro, M.C. Ramirez de Arellano, A.S. Fuentes, J. Org. Chem. 67, 4667 (2002)

    Article  CAS  Google Scholar 

  10. L.S. You, S. Feng, R. An, X.-H. Wang, D.L. Bai, Tetrahedron Lett. 49, 5147 (2008)

    Article  CAS  Google Scholar 

  11. K. Surendra, N.S. Krishnaveni, R. Sridhar, K.R. Rao, Tetrahedron Lett. 47, 2125 (2006)

    Article  CAS  Google Scholar 

  12. R. Kumar, P. Chaudhary, S. Nimesh, R. Chandra, Green Chem. 8, 356 (2006)

    Article  CAS  Google Scholar 

  13. Y.O. Sharma, M.S. Degani, J. Mol. Catal. A 277, 215 (2007)

    Article  CAS  Google Scholar 

  14. M.K. Chaudhuri, S. Hussain, M.L. Kantam, B. Neelima, Tetrahedron Lett. 46, 8329 (2005)

    Article  CAS  Google Scholar 

  15. B.C. Ranu, S. Banerjee, Tetrahedron Lett. 48, 141 (2007)

    Article  CAS  Google Scholar 

  16. Z. Duan, X.-J. Xuan, T. Li, C.-F. Yang, Y.-J. Wu, Tetrahedron Lett. 47, 5433 (2006)

    Article  CAS  Google Scholar 

  17. M.J. Bhanushali, N.S. Nandurkar, S.R. Jagtap, B.M. Bhanage, Catal. Commun. 9, 1189 (2008)

    Article  CAS  Google Scholar 

  18. A.-G. Ying, M. Zheng, H.-D. Xu, F.-L. Qiu, C.-H. Ge, Res. Chem. Intermed. 37, 883 (2011)

    Article  CAS  Google Scholar 

  19. A.-G. Ying, L. Liu, G.-F. Wu, G. Chen, X.-Z. Chen, W.-D. Ye, Tetrahedron Lett. 50, 1653 (2009)

    Article  CAS  Google Scholar 

  20. A.-G. Ying, L.-M. Wang, H.-X. Deng, J.-H. Chen, X.-Z. Chen, W.-D. Ye, Arkivoc (XI), 288 (2009)

    Google Scholar 

  21. A.-G. Ying, R.-H. Zheng, C.-L. Wu, H.-D. Liang, C.-H. Ge, H.-J. Jiang, Chin. J. Org. Chem. 31, 1312 (2011)

    CAS  Google Scholar 

  22. G. Hughes, M. Kimura, S.L. Buchwald, J. Am. Chem. Soc. 125, 11253 (2003)

    Article  CAS  Google Scholar 

  23. B. José, C. Humildad, O. Bernardo, F. Santos, G. Vicente, Synthesis 469–473 (1986)

  24. M. Zahouily, W. Bahlaouan, B. Bahlaouan, A. Rayadh, S. Sebti, Arkivoc XIII, 150 (2005)

    Google Scholar 

Download references

Acknowledgments

This work was supported by the Natural Science Foundation of China (No. 21106090).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Anguo Ying.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ying, A., Zhang, Q., Li, H. et al. An environmentally benign protocol: catalyst-free Michael addition of aromatic amines to α,β-unsaturated ketones in glycerol. Res Chem Intermed 39, 517–525 (2013). https://doi.org/10.1007/s11164-012-0575-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-012-0575-0

Keywords

Navigation