Silica gel-supported polyphosphoric acid (PPA-SiO2) catalyzed one-pot multi-component synthesis of 3, 4-dihydropyrimidin-2(1H)-ones and -thiones: An efficient method for the Biginelli reaction

Bulletin of the Korean Chemical Society

Volumn 32, Issue 2, 2011, Pages 656-658

  Zeinali Dastmalbaf, Mohsen ^a   Davoodnia, Abolghasem ^a   Heravi, Majid M ^b   Tavakoli Hoseini, Niloofar ^a   Khojastehnezhad, Amir ^a   Zamani, Hassan Ali ^c  

^a ISLAMIC AZAD UNIVERSITY   (Iran)

^b ALZAHRA UNIVERSITY   (Iran)

^c ISLAMIC AZAD UNIVERSITY   (Iran)

Author keywords

Biginelli reaction; Heterogeneous catalysis; Multi component reactions; PPA SiO2

Indexed keywords

ARYL ALDEHYDES; BIGINELLI REACTION; DIHYDROPYRIMIDIN; EFFICIENT METHOD; ETHYLACETOACETATE; HETEROGENEOUS CATALYSIS; HIGH YIELD; MILD REACTION CONDITIONS; MULTI-COMPONENT REACTIONS; MULTICOMPONENTS; ONE POT; POLYPHOSPHORIC ACIDS; PPA-SIO2; RECYCLABLE CATALYST; SHORT REACTION TIME; THIONES; THREE COMPONENT REACTIONS;

ACETONITRILE; ALDEHYDES; CATALYSIS; CATALYSTS; DRIERS (MATERIALS); SILICA; SILICA GEL; SILICON COMPOUNDS; THIOUREAS; UREA;

SYNTHESIS (CHEMICAL);

EID: 79951941107     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2011.32.2.656     Document Type: Article

References (40)

1. Strubing, D.; Neumann, H.; Klaus, S.; Hubner, S.; Beller, M. Tetrahedron 2005, 61, 11333.
2. Heydari, A.; Arefi, A.; Khaksar, S.; Shiroodi, R. K. J. Mol. Catal. A: Chem. 2007, 271, 142.
3. Yu, L.; Chen, B.; Huang, X. Tetrahedron Lett. 2007, 48, 925.
4. Kappe, C. O.; Fabian, W. W. Tetrahedron 1997, 53, 2803.
5. Mayer, T. U.; Tapoor, T. M.; Haggarty, S. J.; King, R. W.; Schreiber, S. L.; Mitchison, T. J. Science 1999, 286, 971.
6. Kappe, C. O. Eur. J. Med. Chem. 2000, 35, 1043.
7. Rovnyak, G. C.; Kimball, S. D.; Beyer, B.; Cucinotta, G.; Dimarco, D. J.; Gougoutas, J.; Hedberg, A.; Malley, M.; Mccarthy, J. P.; Zhang, R.; Mareland, S. J. Med. Chem. 1995, 38, 119.
8. Grover, G. J.; Dzwomczyk, S.; Mcmullen, D. M.; Normadinam, C. S.; Sleph, P. G.; Moreland, S.; Cardiovasc, J. Pharmacol. 1995, 26, 289.
9. Biginelli, P. Gazz. Chim. Ital. 1893, 23, 360.
10. Barluenga, J.; Thomas, M.; Ballesterus, A.; Lopez, A. Tetrahedron Lett. 1989, 30, 4573.
11. Gupta, R.; Gupta, A. K.; Paul, S.; Kachroo, P. L. Indian J. Chem. Sect. B 1995, 34B, 151.
12. Yadav, J. S.; Reddy, B. V. S.; Reddy, E. J.; Ramalingam, T. J. Chem. Res. (S) 2000, 354.
13. Tu, S.; Fang, F.; Miao, C.; Jiang, H.; Feng, Y.; Shi, D.; Wang, X. Tetrahedron Lett. 2003, 44, 6153.
14. Jin, T.; Zhang, S.; Li, T. Synth. Commun. 2002, 32, 1847.
15. Salehi, P.; Dabiri, M.; Zolfigol, M. A.; Bodaghi Fard, M. A. Tetrahedron Lett. 2003, 44, 2889.
16. Ma, Y.; Qian, C.; Wang, L.; Yang, M. J. Org. Chem. 2000, 65, 3864.
17. Su, W.; Li, J.; Zheng, Z.; Shen, Y. Tetrahedron Lett. 2005, 46, 6037.
18. Heravi, M. M.; Behbahani, F. K.; Oskooie, H. A. Chin. J. Chem. 2008, 26, 2203.
19. Fu, N. Y.; Yuan, Y. F.; Cao, Z.; Wang, S. W.; Wang, J. T.; Peppe, C. Tetrahedron 2002, 58, 4801.
20. Ranu, B. C.; Hajra, A.; Jana, U. J. Org. Chem. 2000, 65, 6270.
21. Varala, R.; Alam, M. M.; Adapa, S. R. Synlett 2003, 67.
22. Hajipour, A. R.; Ruoho, A. E. Tetrahedron Lett. 2005, 46, 8307.
23. Kantevari, S.; Bantu, R.; Nagarapu, L. J. Mol. Catal. A: Chem. 2007, 269, 53.
24. Shaterian, H. R.; Hosseinian, A.; Ghashang, M. Arkivoc. 2009, Part 2, 59.
25. Davoodnia, A.; Bakavoli, M.; Vahedinia, A.; Rahimizadeh, M.; Roshani, M. Heterocycles 2006, 68, 801.
26. Davoodnia, A.; Bakavoli, M.; Pooryaghoobi, N.; Roshani, M. Heterocycl. Commun. 2007, 13, 323-325.
27. Davoodnia, A.; Roshani, M.; Saleh-Nadim, E.; Bakavoli, M.; Tavakoli-Hoseini, N. Chin. Chem. Lett. 2007, 18, 1327-1330.
28. Davoodnia, A.; Behmadi, H.; Zare-Bidaki, A.; Bakavoli, M.; Tavakoli-Hoseini, N. Chin. Chem. Lett. 2007, 18, 1163.
29. Davoodnia, A.; Bakavoli, M.; Mohseni, Sh.; Tavakoli-Hoseini, N. Monatsh. Chem. 2008, 139, 963.
30. Davoodnia, A.; Bakavoli, M.; Barakouhi, Gh.; Tavakoli-Hoseini, N. Chin. Chem. Lett. 2007, 18, 1483.
31. Davoodnia, A.; Roshani, M.; Malaeke, S. H.; Bakavoli, M. Chin. Chem. Lett. 2008, 19, 525.
32. Davoodnia, A.; Heravi, M. M.; Rezaei-Daghigh, L.; Tavakoli-Hoseini, N. Monatsh. Chem. 2009, 140, 1499.
33. Davoodnia, A.; Bakavoli, M.; Moloudi, R.; Khashi, M.; Tavakoli-Hoseini, N. Chin. Chem. Lett. 2010, 21, 1.
34. Davoodnia, A.; Bakavoli, M.; Moloudi, R.; Khashi, M.; Tavakoli-Hoseini, N. Monatsh. Chem. 2010, 141, 867.
35. Davoodnia, A.; Heravi, M. M.; Safavi-Rad, Z.; Tavakoli-Hoseini, N. Synth. Commun. 2010, 40, 2588.
36. Davoodnia, A.; Heravi, M. M.; Rezaei-Daghigh, L.; Tavakoli-Hoseini, N. Chin. J. Chem. 2010, 28, 429.
37. Davoodnia, A.; Allameh, S.; Fakhari, A. R.; Tavakoli-Hoseini, N. Chin. Chem. Lett. 2010, 21, 550.
38. Tavakoli-Hoseini, N.; Davoodnia, A. Asian J. Chem. 2010, 22, 7197.
39. Davoodnia, A. Asian J. Chem. 2010, 22, 1595.
40. Aoyama, T.; Takido, T.; Kodomari, M. Synlett. 2004, 13, 2307.