Abstract
Bismuth(III) nitrate pentahydrate is found as a mild and highly efficient catalyst for the rapid synthesis of 4-amino-5-pyrimidine carbonitrile and pyrimidinone derivatives via three-component reaction of aldehydes, N-unsubstituted amidines, and malononitrile or ethyl cyanoacetate under thermal aqueous conditions. The reaction protocol is rapid and simple which is followed by formation of the corresponding pyrimidine and pyrimidinone derivatives in good to excellent yields with high purity.
Similar content being viewed by others
References
S.F. Wnuk, E. Lewandowska, D.R. Companioni, P.I. García Jr., J.A. Secrist III, Org. Biomol. Chem 2, 120 (2004)
N.A. Hassan, Molecules 5, 826 (2000)
M. Pemmsin, C. Lnu-Due, F. Hoguet, C. Gaultier, J. Narciss, Eur. J. Chem. 23, 543 (1988)
A. Cannito, M. Pemmsin, C. Lnu-Due, F. Hoguet, C. Gaultier, J. Narcisse, Eur. J. Chem. 25, 635 (1990)
P.A.S. Smith, R.O. Kan, J. Org. Chem. 29, 2261 (1964)
S. Nega, J. Aionso, A. Diazj, F. Junquere, J. Heterocycl. Chem. 27, 269 (1990)
C.J. Shishoo, K.S. Jain, J. Heterocycl. Chem. 29, 883 (1992)
J.U.S. Peters, D. Hunziker, H. Fischer, M. Kansy, S. Weber, S. Kritter, A. Muller, F. Ricklin, M. Boehringer, S.M. Poli, M. Csato, B.M. Loeffler, Bioorg. Med. Chem. Lett. 14, 3575 (2004)
H. Hattori, Heterogeneous basic catalysis. Chem. Rev. 95, 537 (1995)
B.K. Banik, A.T. Reddy, A. Datta, C. Mukhopadhyay, Tetrahedron Lett. 48, 7392 (2007)
I. Mohammadpoor-Baltork, M.M. Khodaei, K. Nikoofar, Tetrahedron Lett. 44, 591 (2003)
S. Samajdar, F.F. Becker, B.K. Banik, Tetrahedron Lett. 41, 8017 (2000)
B.K. Banik, N. Srivastava, S.K. Dasgupta, Tetrahedron Lett. 44, 1191 (2003)
B.K. Banik, N. Srivastava, J. Org. Chem. 68, 2109 (2003)
S.D. Samant, V.M. Alexander, R.P. Bhat, Tertrahedron Lett. 46, 6957 (2005)
S. Cunha, M.T. Rodrigues, Tertrahedron Lett. 47, 6955 (2006)
H. Sheibani, A. Saljoogi, A.S. Bazgir, Arkivoc. 2, 115 (2008)
H. Sheibani, M. Seifi, A. Bazgir, Synth. Commun. 39, 1055 (2009)
H. Sheibani, F. Hassani, J. Heterocycl. Chem. 48, 915 (2011)
M. Seifi, H. Sheibani, Catal. Lett. 126, 275 (2008)
Acknowledgment
The authors express appreciation to the Shahid Bahonar University of Kerman Faculty Research Committee Fund for its support of this investigation.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Zahedifar, M., Sheibani, H. Rapid three-component synthesis of pyrimidine and pyrimidinone derivatives in the presence of Bi(NO3)3·5H2O as a mild and highly efficient catalyst. Res Chem Intermed 41, 105–111 (2015). https://doi.org/10.1007/s11164-013-1172-6
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11164-013-1172-6