Abstract
An operationally simple, atom-economical, and green procedure has been developed for the synthesis of dihydropyridine derivatives by a simple condensation of barbituric acid, aldehyde, and ammonium acetate in water under catalyst-free conditions. Excellent yields and purity were obtained with only filtration and washing with hot water and ethanol.
Similar content being viewed by others
References
J.R. Quinn, S.C. Zimmerman, Org. Lett. 6, 1649 (2004)
S. Djurdjevic, D.A. Leigh, H. McNab, S. Parsons, G. Teobaldi, F. Zerbetto, J. Am. Chem. Soc. 129, 476 (2007)
J. Taubitz, U. Lüning, Eur. J. Org. Chem. 35, 5922–5927 (2008)
Z.S. Derewenda, U. Derewenda, P.M. Kobos, J. Mol. Biol. 241, 83–93 (1994)
J. Bellaf, H.M. Bermanf, J. Mol. Biol. 264, 734–742 (1996)
P. Chakrabarti, S. Chakrabarti, J. Mol. Biol. 284, 867–873 (1998)
Z. Berkovitch-Yellin, L. Leiserowitz, Acta. Cryst. B 40, 159–165 (1984)
L.J.W. Shimon, M. Vaida, L. Addadi, M. Lahav, L. Leiserowitz, J. Am. Chem. Soc. 112, 6215–6220 (1990)
G.R. Desiraju, Angew. Chem. Int. Ed. 34, 2311–2327 (1995)
K.N. Houk, S. Menzer, S.P. Newton, R.M. Raymo, J.F. Stoddart, D.J. Williams, J. Am. Chem. Soc. 121, 1479–1487 (1999)
R.A. Musah, G.M. Jensen, R.J. Rosenfeld, D.E. McRee, D.B. Goodin, J. Am. Chem. Soc. 119, 9083–9084 (1997)
G. Cooke, V.M. Rotello, Chem. Soc. Rev. 31, 275–286 (2002)
M. Kidwai, S. Saxena, M.K. Rahman Khan, S.S. Thukral, Bioorg. Med. Chem. Lett. 15, 4295–4298 (2005)
M. Kidwai, K. Singhal, J. Heterocycl Chem. 44, 1253–1257 (2011)
S.V. Chankeshwara, A.K. Chakraborti, Org. Lett. 8, 3259–3262 (2006)
G.L. Khatik, R. Kumar, A.K. Chakraborti, Org. Lett. 8, 2433–2436 (2006)
N. Azizi, M.R. Saidi, Org. Lett. 7, 3649–3651 (2005)
N. Azizi, F. Aryanasab, L. Torkiyan, A. Ziyaei, M.R. Saidi, J. Org. Chem. 71, 3634–3635 (2006)
N. Azizi, L. Torkiyan, M.R. Saidi, Org. Lett. 8, 2079–2082 (2006)
N. Azizi, F. Aryanasab, M.R. Saidi, Org. Lett. 8, 5275–5278 (2006)
A.R. Khajeh Amiri, N. Azizi, M. Bolourtchian, M.R. Saidi, Synlett 14, 2245–2248 (2009)
A.R. Khajeh Amiri, N. Azizi, M. Bolourtchian, Mol. Divers. 15(1), 157–161 (2011)
M.M. Sanchez Duque, C. Allais, N. Isambert, T. Constantieux, J. Rodriguez, Top. Heterocycl. Chem. 23, 227–277 (2010)
G. Bartoli, M. Bosco, P. Galzerano, R. Giri, A. Mazzanti, P. Melchiorre, L. Sambri, Eur. J. Org. Chem. 2008(23), 3970–3975 (2008)
M. Kidwaia, K. Singhala, Synth. Commun. 36, 1887–1891 (2006)
R.A. Mekheimer, A.A. Hameed, K. Sadek, Green Chem. 10, 592–593 (2008)
J.S. Yadav, B.V.S. Reddy, A.K. Basak, A.V. Narsaiah, Green Chem. 5, 60–63 (2003)
M. Kidwai, K. Singhal, Can. J. Chem. 85, 400–405 (2007)
K. Singh, J. Singh, H. Singh, Tetrahedron 54, 935–942 (1998)
S.D. Sharma, P. Hazarika, D. Konwar, Catal. Commun. 9, 709–714 (2008)
S. Koa, C.F. Yao, Tetrahedron 62, 7293–7299 (2006)
P. Gupta, S. Gupta, R.L. Sharma, Indian J. Chem. Sect. B Org. Chem. Incl. Med. Chem. 48, 1187–1194 (2009)
Acknowledgments
The financial support of this work provided by Chemistry and Chemical Research Center of Iran and Iran National Science Foundation (INSF) is gratefully appreciated.
Author information
Authors and Affiliations
Corresponding authors
Electronic supplementary material
Experimental details and spectroscopic characterization (copy of 1H and 13C NMR and mass) of all compounds.
Rights and permissions
About this article
Cite this article
Azizi, N., Mobinikhaledi, A., Amiri, A.K. et al. Catalyst-free synthesis of dihydropyridine from barbituric acid in water. Res Chem Intermed 38, 2271–2275 (2012). https://doi.org/10.1007/s11164-012-0543-8
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11164-012-0543-8