Abstract
A new and efficient one-pot synthesis of dihydropyridones derivatives by four-component reaction between cyanoacetamide, aryl aldehydes, and ethyl acetoacetate with ammonium carbonate is described. The reactions were performed in water and ethanol under reflux conditions and afforded high yields of products.
Graphical abstract
Similar content being viewed by others
References
M. Misic-Vukovic, D. Mijin, M. Radojkovic-Velickovic, N. Valentic, V. Krstic, J. Serb. Chem. Soc. 63, 585 (1998)
M. Balasubramanian, J.G. Keay, A.R. Katritzky, C.W. Rees, E.V.F. Scriven, Comprehensive Heterocyclic Chemistry II, Vol 5, (Pergamon Press, London 1996), pp. 245–300 Chapter 6
E.C. Constable, C.E. Housecroft, M. Neuburger, D. Phillips, P.R. Raithby, E. Schofield, E. Sparr, D.A. Tocher, M. Zehnder, Y. Zimmermann, J. Chem. Soc. Dalton Trans., 13, 2219 (2000)
B.Y. Kim, J.B. Ahn, H.W. Lee, S.K. Kang, J.H. Lee, J.S. Shin, S.K. Ahn, C.I. Hong, S.S. Yoon, Eur. J. Med. Chem. 39, 433 (2004)
I.J. Enyedy, S. Sakamuri, W.A. Zaman, K.M. Johnson, S. Wang, Bioorg. Med. Chem. Lett. 13, 513 (2003)
A.D. Pillai, P.D. Rathod, P.X. Franklin, M. Patel, M. Nivsarkar, K.K. Vasu, H. Padh, V. Sudarsanam, Biochem. Biophys. Res. Commun. 301, 183 (2003)
V. Klimešová, M. Svoboda, K. Waisser, M. Pour, J. Kaustová, II Farmaco 54, 666 (1999)
G. Jones, A.R. Katritzky, C.W. Rees, E.V.F. Scriven, Editors, Comprehensive Heterocyclic Chemistry II Vol. 5, Pergamon Press, London (1996), pp. 168–243 Chapter 5, and references cited therein
A.R. Katritzky, A.A.A. Abdel-Fattah, D.O. Tymoshenko, S.A. Essawy, Synthesis, 80, 2114 (1999)
Acknowledgments
We gratefully acknowledge financial support from the Research Council of Islamic Azad University of Yazd of Iran.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Dehghan, A., Singh, S., Anary-Abbasinejad, M. et al. Four-component reaction between cyanoacetamide, aryl aldehydes, and ethyl acetoacetate with ammonium carbonate. Res Chem Intermed 41, 1001–1009 (2015). https://doi.org/10.1007/s11164-013-1250-9
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11164-013-1250-9