One-pot chemoselective synthesis of novel fused pyrimidine derivatives
Article
First Online:
Received:
- 394 Downloads
- 8 Citations
One-pot triple-component reaction of 4-hydroxycoumarin with aromatic aldehydes and 2-aminobenzimidazole, 3-amino-1H-1,2,4-triazole, or 6-aminouracil in acetonitrile in the presence of catalytic amounts of sulfamic acid led to a chemoselective synthesis of chromeno[4,3-d]pyrimidine-6-one, triazolo[1,5-a]pyrimidin-5-one, and pyrido[2,3-d]-pyrimidine-2,4,7-trione derivatives, respectively, in good yields.
Keywords
chromeno[4,3-d]pyrimidinones pyrido[2,3-d]pyrimidine-2,4,7-triones pyrimidine derivatives sulfamic acid triazolo[1,5-a]pyrimidin-5-ones multicomponent reactionNotes
We gratefully acknowledge partial financial support from the Alzahra University Research Council.
References
- 1.L. F. Tietze, Chem. Rev., 96, 115 (1996).CrossRefGoogle Scholar
- 2.A. Dömling, Chem. Rev., 106, 17 (2006).CrossRefGoogle Scholar
- 3.L. Weber, Drug Discovery Today, 7, 143 (2002).Google Scholar
- 4.A. Dömling, Curr. Opin. Chem. Biol., 6, 306 (2002).CrossRefGoogle Scholar
- 5.G. Guillena, D. J. Ramon, and M. Yus, Tetrahedron: Asymmetry, 18, 693 (2007).CrossRefGoogle Scholar
- 6.V. Nair, C. Rajesh, A. U. Vinod, S. Bindu, A. R. Sreekanth, J. S. Mathen, and L. Balagopal, Acc. Chem. Res., 36, 899 (2003).CrossRefGoogle Scholar
- 7.Y. Fellahi, P. Dubois, V. Agafonov, F. Moussa, J. E. Ombetta-Goka, J. Guenzet, and Y. Frangin, Bull. Soc. Chim. Fr., 133, 869 (1996).Google Scholar
- 8.J. Kempson, W. J. Pitts, J. Barbosa, J. Guo, O. Omotoso, A. Watson, K. Stebbins, G. C. Starling, J. H. Dodd, J. C. Barrish, R. Felix, and K. Fischer, Bioorg. Med. Chem. Lett., 15, 1829 (2005).CrossRefGoogle Scholar
- 9.O. Bruno, C. Brullo, S. Schenone, F. Bondavalli, A. Ranise, M. Tognolini, M. Impicciatore, V. Ballabeni, and E. Barocelli, Bioorg. Med. Chem., 14, 121 (2006).CrossRefGoogle Scholar
- 10.A. V. Ivachtchenko, E. S. Golovina, M. G. Kadieva, A. G. Koryakova, S. M. Kovalenko, O. D. Mitkin, I. M. Okun, I. M. Ravnyeyko, S. E. Tkachenko, and O. V. Zaremba, Bioorg. Med. Chem., 18, 5282 (2010).CrossRefGoogle Scholar
- 11.S. A. Said, A. E.-G. Amr, N. M. Sabry, and M. M. Abdalla, Eur. J. Med. Chem., 44, 4787 (2009).CrossRefGoogle Scholar
- 12.M. M. A. El-Gendy, M. Shaaban, K. A. Shaaban, A. M. El-Bondkly, and H. Laatsch, J. Antibiot., 61, 149 (2008).CrossRefGoogle Scholar
- 13.R. Magan, C. M. J. M. Salas, M. Barrera-Perez, M. J. Rosales, and M. Sanchez-Moreno, Mem. Inst. Oswaldo Cruz, 99, 651 (2004).CrossRefGoogle Scholar
- 14.I. Lakomska, Inorg. Chim. Acta, 362, 669 (2009).CrossRefGoogle Scholar
- 15.A.-R. B. A. El-Gazzar, M. M. El-Enany, and M. N. Mahmoud, Bioorg. Med. Chem., 16, 3261 (2008).CrossRefGoogle Scholar
- 16.M. Saeedi, M. M. Heravi, Y. S. Beheshtiha, and H. A. Oskooie, Tetrahedron, 66, 5345 (2010).CrossRefGoogle Scholar
- 17.M. M. Heravi, M. Saeedi, Y. S. Beheshtiha, and H. A. Oskooie, Mol. Diversity, 15, 239 (2011).CrossRefGoogle Scholar
- 18.M. M. Heravi, M. Saeedi, Y. S. Beheshtiha, and H. A. Oskooie, Heterocycles, 83, 535 (2011).CrossRefGoogle Scholar
- 19.M. M. Heravi, B. Baghernejad, and H. A. Oskooie, Curr. Org. Chem., 13, 1002 (2009).Google Scholar
Copyright information
© Springer Science+Business Media, Inc. 2011