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.
Similar content being viewed by others
References
A. Corma, S. Iborra, A. Velty, Chem. Rev. 107, 2411 (2007)
N. Armaroli, V. Balzani, Angew. Chem. Int. Ed. 46, 52 (2007)
A. Wolfson, C. Dlugy, Y. Shotland, Environ. Chem. Lett. 5, 67 (2007)
A. Wolfson, C. Dlugy, Chem. Pap. 61, 228 (2007)
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)
F. He, P. Li, Y.-L. Gu, G.-X. Li, Green Chem. 11, 1767 (2009)
Y.-F. Wang, T. Izawa, S. Kobayashi, M. Ohno, J. Am. Chem. Soc. 104, 6465 (1982)
Y. Hayashi, J.J. Rode, E.J. Corey, J. Am. Chem. Soc. 118, 5502 (1996)
S. Fustero, B. Pina, E. Salavert, A. Navarro, M.C. Ramirez de Arellano, A.S. Fuentes, J. Org. Chem. 67, 4667 (2002)
L.S. You, S. Feng, R. An, X.-H. Wang, D.L. Bai, Tetrahedron Lett. 49, 5147 (2008)
K. Surendra, N.S. Krishnaveni, R. Sridhar, K.R. Rao, Tetrahedron Lett. 47, 2125 (2006)
R. Kumar, P. Chaudhary, S. Nimesh, R. Chandra, Green Chem. 8, 356 (2006)
Y.O. Sharma, M.S. Degani, J. Mol. Catal. A 277, 215 (2007)
M.K. Chaudhuri, S. Hussain, M.L. Kantam, B. Neelima, Tetrahedron Lett. 46, 8329 (2005)
B.C. Ranu, S. Banerjee, Tetrahedron Lett. 48, 141 (2007)
Z. Duan, X.-J. Xuan, T. Li, C.-F. Yang, Y.-J. Wu, Tetrahedron Lett. 47, 5433 (2006)
M.J. Bhanushali, N.S. Nandurkar, S.R. Jagtap, B.M. Bhanage, Catal. Commun. 9, 1189 (2008)
A.-G. Ying, M. Zheng, H.-D. Xu, F.-L. Qiu, C.-H. Ge, Res. Chem. Intermed. 37, 883 (2011)
A.-G. Ying, L. Liu, G.-F. Wu, G. Chen, X.-Z. Chen, W.-D. Ye, Tetrahedron Lett. 50, 1653 (2009)
A.-G. Ying, L.-M. Wang, H.-X. Deng, J.-H. Chen, X.-Z. Chen, W.-D. Ye, Arkivoc (XI), 288 (2009)
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)
G. Hughes, M. Kimura, S.L. Buchwald, J. Am. Chem. Soc. 125, 11253 (2003)
B. José, C. Humildad, O. Bernardo, F. Santos, G. Vicente, Synthesis 469–473 (1986)
M. Zahouily, W. Bahlaouan, B. Bahlaouan, A. Rayadh, S. Sebti, Arkivoc XIII, 150 (2005)
Acknowledgments
This work was supported by the Natural Science Foundation of China (No. 21106090).
Author information
Authors and Affiliations
Corresponding author
Rights 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
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11164-012-0575-0