Mesoporous molecular sieve MCM-41 catalyzed one-pot synthesis of 3,4-dihydro-2(1H)-pyrimidinones and -thiones under solvent-free conditions

Bulletin of the Chemical Society of Ethiopia

Volumn 25, Issue 2, 2011, Pages 309-313

  Hekmatshoar, Rahim ^a   Heidari, Maryam ^a   Heravi, Majid M ^a   Baghernejad, Bita ^a  

^a ALZAHRA UNIVERSITY   (Iran)

Author keywords

Biginelli reaction; Dihydropyrimidinones; MCM 41; One pot; Reusable

Indexed keywords

EID: 79960169800     PISSN: 10113924     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (41)

1. Rovnyak, G.C.; Kimball, S.D.; Beyer, B.; Cucinotta, G.; Dimarco, J.D.; Gougoutas, J.; Hedderg, A.; Malley, M.; MacCarthy, J.P.; Zhang, R.; Moreland, S. J. Med. Chem. 1995, 38, 119.
2. Atwal, K.S.; Rovnyak, G.C.; Kimball, S.D.; Floyd, D.M.; Moreland, S.; Swanson, B.; Gougoutas, S.J.; Schwartz, J.; Amillie, K.M.; Malley, M.F. J. Med. Chem. 1990, 33, 2629.
3. Atwal, K.S.; Swanson, B.N.; Unger, S.E.; Floyd, D.M.; Moreland, S.; Hedderg, A.; O'Reilly, B.C. J. Med. Chem. 1991, 34, 806.
4. Kappe, C.O. Tetrahedron 1993, 49, 6737.
5. Snider, B.B.; Shi, Z.J. J. Org. Chem. 1993, 58, 3828.
6. Patil, A.D.; Kumar, N.V.; Kokke, W.C.; Bean, M.F.; Freyer, A.J.; De Brosse, C.; Mai, S.; Truneh, A.; Faulkner, D.J.; Carte, B.; Breen, A.L.; Hertzberg, R.P.; Johnson, R.K.; Westley, J.W.; Potts, B.C. J. Org. Chem. 1995, 60, 1182.
7. Snider, B.B.; Chen, J.; Patil, A.D.; Freyer, A. Tetrahedron Lett. 1996, 37, 6977.
8. Rama Rao, A.V.; Gujar, M.; Vasudevan, J. J. Chem. Soc. Chem. Commun. 1995, 1369.
9. Hu, E.H.; Sidler, D.R.; Dolling, U. J. Org. Chem. 1998, 63, 3454.
10. Lu, J.; Ma, M. Synlett 2000, 1, 63.
11. Ranu, B.C.; Hajra, A.; Jana, H. J. Org. Chem. 2000, 65, 6270.
12. Reddy, V.; Mahesh, M.; Raju, P.V.; Babu, T.; Reddy, V.V. Tetrahedron Lett. 2000, 43, 2657.
13. Ramalinga, K.; Vijayalaxmi, P.; Kaimal, T. Synlett 2001, 6, 863.
14. Kumar, A.K.; Kasthuraiah, M.S.; Reddy, C. Tetrahedron Lett. 2001, 42, 7873.
15. Yadav, J.S.; Reddy, B.V.; Srinivas, R.; Venugopal, C.; Ramalingam, T. Synthesis 2001, 4, 1341.
16. Maity, G.H.; Kundu, P.; Guin, C.; Roy, S.C. Tetrahedron Lett. 2003, 44, 2757.
17. Kresege, C.T.; Leonowicz, M.E.; Roth, W.J.; Vartadi, J.C.; Beck, J.S. Nature 1992,710.
18. Beck, J.S.; Vartuli, J.C.; Roth, W.J.; Leonowicz, M.E.; Kresege, C.T.; Schmitt, K.D.; Chu, C.T.; Olson, D.H.; Sheppard, E.W.; Mccullen, S.B.; Higgius, J.B.; Schlenker, J.L. J. Am. Chem. Soc. 1992, 114, 10834.
19. Corma, A. Chem. Rev. 1997, 97, 2373.
20. Beck, J.S.; Vartuli, J.C.; Curr. O. Solid State Mater. Sc. 1996, 1, 76.
21. Zhao, X.S.; Lu, G.Q.; Millar, G.J. Ind. Eng. Chem. Res. 1996, 35, 2075.
22. Namba, S.; Mochizuki, A.; Kito, M. Stud. Surf. Sci. Catal. 1998, 17, 257.
23. Jaroniec, M.; Kruk, M.; June Shin, H.; Ryoo, R.; Sakamoto, Y.; Terasaki, O. Micropor. Mesopor. Mater. 2001, 48, 127.
24. Farzaneh, F.; Soleimannejad, J.; Ghandi, M. J. Mol. Catal. A. Chem. 1997, 118, 223.
25. Farzaneh, F.; Ghandi, M.; Soleimannejad, J. J. Mol. Catal. A. Chem. 2000, 192, 103.
26. Bamoharram, F.F.; Heravi, M.M.; Roshani, M.; Gjarib, A.; Jahangiri, M. Appl. Catal. 2006, 302, 42.
27. Heravi, M.M.; Hekmatshoar, R.; Pedram, L. J. Mol. Catal. A: Chem. 2005, 89, 231.
28. Tajbakhsh, M.; Mohajerani, B.; Heravi, M.M.; Ahmadi, A.N. J. Mol. Catal. A: Chem. 2005, 236, 216.
29. Heravi, M.M.; Bakhtiari, K.; Bamoharram, F.F. Catal. Commun. 2006, 7, 373.
30. Gohain, M.; Prajapati, D.; Jagir, S. Synlett 2004, 2, 235.
31. Narsaiah, A.; Basak, A.K.; Nagaiah, K. Synthesis 2004, 8, 1253.
32. Kappe, C.O.; Kumar, D.; Varma, R.S. Synthesis 1999, 10, 1799.
33. Biginelli, P. Gazz. Chim. Ital. 1893, 23, 360.
34. Rani, R.V.; Srinivas, N.; Kishan, M.R.; Kulkarni, S.J.; Raghavan, K.V. Green Chem. 2001, 3, 305.
35. Bigi, F.; Carloni, S.; Frullanti, B.; Maggi, R.; Sartori, G. Tetrahedron Lett. 1999, 40, 3465.
36. Fu, N.-Y.; Yuan, Y.-F.; Cao, Z.; Wang, S.-W.; Wang, J.-T.; Peppe, C. Tetrahedron 2002, 58, 4801.
37. Heravi, M.M.; Derikvand, F.; Bamoharram, F. J. Mol. Cata. A: Chem. 2005, 242, 173.
38. Tajbakhsh, M.; Mohajerani, B.; Heravi, M.M.; Ahmadi, A.N. J. Mol. Catal. A: Chem. 2005, 236, 216.
39. Lu, J.; Bai, Y.; Wang, Z.; Yang, B.; Ma, H. Tetrahedron Lett. 2000, 41, 9075.
40. Kassaee, M.; Masrouri, H.; Movahedi, F.; Mohammadi, R. Helv. Chim. Acta 2010, 93, 261.
41. Zhao, X.S.; Lu, G.Q.; Hu, X. Micropor. Mesopor. Mater. 2000, 41, 37.