A practical and green approach towards synthesis of dihydropyrimidinones: Using heteropoly acids as efficient catalysts

Bioorganic and Medicinal Chemistry Letters

Volumn 16, Issue 9, 2006, Pages 2463-2466

  Rafiee, Ezzat ^a   Jafari, Hadi ^a  

^a RAZI UNIVERSITY   (Iran)

Author keywords

Biginelli reaction; Dihydropyrimidinones or thiones (DHPMs); Heteropoly acid; Multicomponent reactions (MCR)

Indexed keywords

DIHYDROPYRIMIDINONE DERIVATIVE; PYRIMIDINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIGINELLI REACTION; CATALYST; CHEMICAL STRUCTURE; POLYMERIZATION; REACTION TIME; SUBSTITUTION REACTION; SYNTHESIS;

ACIDS; CATALYSIS; CYCLIZATION; MOLECULAR STRUCTURE; PYRIMIDINONES; STEREOISOMERISM;

EID: 33644989059     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2006.01.087     Document Type: Article

References (55)

1. R.W. Armstrong, A.P. Combs, P.A. Tempest, S.D. Brown, and T.A. Keating Acc. Chem. Res. 29 1996 123
2. L.F. Tietze, and M.E. Lieb Curr. Opin. Chem. Biol. 2 1998 363
3. S.L. Dax, J.J. McNally, and M.A. Youngman Curr. Med. Chem. 6 1999 255
4. M. Plunkett, and J.A. Ellman New Drugs Sci. Am. 1997 276
5. S.L. Schreiber Science 287 2000 1964
6. C.O. Kappe Acc. Chem. Res. 33 2000 879
7. L. Weber, K. Illgen, and M. Almstetter Synlett 3 1999 366
8. C.O. Kappe Tetrahedron 49 1993 6937
9. C.O. Kappe Eur. J. Med. Chem. 35 2000 1043
10. G.C. Rovnyak, S.D. Kimball, B. Beyer, G. Cucinotta, D.J. Dimarco, J. Gougoutas, A. Hedberg, M. Malley, J.P. McCarthy, R. Zhang, and S. Moreland J. Med. Chem. 38 1995 119
11. K.S. Atwal, B.N. Swanson, S.E. Unger, D.M. Floyd, S. Moreland, A. Hedberg, and B.C. O'Reilly J. Med. Chem. 34 1991 806
12. G.J. Grover, S. Dzwomczyk, D.M. McMullen, C.S. Normadinam, P.G. Sleph, and S.J. Moreland J. Cardiovasc. Pharmacol. 26 1995 289
13. Silder, D. R.; Larsen, R. D.; Chartrain, M.; Ikemote, N.; Roerber, C. M.; Taylor, C. S.; Li, W.; Bills, G. F. PCT Int. WO 99 07695.
14. C.O. Kappe, W.M.F. Fabian, and M.A. Semones Tetrahedron 53 1997 2803
15. Bruce, M. A.; Pointdexter, G. S.; Johnson, G. PCT Int. Appl. WO 98 33791.
16. A.D. Patil, N.V. Kumar, W.C. Kokke, M.F. Bean, A.J. Freyer, C. Debrossi, S. Mai, A. Truneh, D.J. Faulkner, B. Carte, A.L. Breen, R.P. Hertzberg, R.K. Johnson, J.W. Westley, and B.C.M. Potts J. Org. Chem. 60 1995 1182
17. A.V. Rama Rao, M.K. Gujar, and J. Vasudevan J. Chem. Soc., Chem. Commun. 1995 1369
18. B.B. Snider, J. Chen, A.D. Patil, and A. Freyer Tetrahedron Lett. 37 1996 6977
19. D.S. Bose, M. Sudharshan, and S.W. Chavhan ARKIVOC 2005 228
20. D. Russowsky, F.A. Lopes, V.S.S. da Silva, K.F.S. Canto, M.G. Montes D'Oca, and M.N. Godoi J. Brazil. Chem. Soc. 15 2004 165
21. Y.T. Reddy, B. Rajitha, P.N. Reddy, B.S. Kumar, and V.P. Rao Synth. Commun. 34 2004 3821
22. A.S. Paraskar, G.K. Dewkar, and A. Sudalai Tetrahedron Lett. 44 2003 3305
23. J. Lu, and Y. Bai Synthesis 2002 466
24. J.S. Yadav, B.V.S. Reddy, R. Srinivas, C. Venugopal, and T. Ramalingam Synthesis 2001 1341
25. Y. Ma, C. Qian, L. Wang, and M. Yang J. Org. Chem. 65 2000 3864 and references cited therein
26. E.H. Hu, D.R. Sidler, and U.H. Dolling J. Org. Chem. 63 1998 3454
27. B.C. Ranu, A. Hajra, and U. Jana J. Org. Chem. 65 2000 6270
28. C.V. Reddy, M. Mahesh, P.V.V.K. Raju, T.R. Babu, and V.V.N. Reddy Tetrahedron Lett. 43 2002 2657
29. N.Y. Fu, Y.F. Yuan, Z. Cao, S.W. Wang, J.T. Wang, and C. Peppe Tetrahedron 58 2002 4801
30. D.S. Bose, L. Fatima, and H.B. Mereyala J. Org. Chem. 68 2003 587
31. K. Ramalinga, P. Vijayalakshmi, and T.N.B. Kaimal Synlett 2001 863
32. C.O. Kappe, D. Kumar, and R.S. Varma Synthesis 1999 1799
33. P. Salehi, M. Dabiri, M.A. Zolfigol, and M.A. Bodaghi Fard Tetrahedron Lett. 44 2003 2889
34. E. Rafiee, S. Tangestaninejad, M.H. Habibi, and V. Mikhani Bioorg. Med. Chem. Lett. 14 2004 3611
35. E.F. Kozhevnikova, E. Rafiee, and I.V. Kozhevnikov Appl. Catal., A 260 2004 25
36. E. Rafiee, S. Tangestaninejad, M.H. Habibi, and V. Mikhani Bull. Korean Chem. Soc. 25 2004 599
37. E. Rafiee, S. Tangestaninejad, M.H. Habibi, and V. Mikhani Synth. Commun. 34 2004 3673
38. E. Rafiee, F. Tork, and M. Joshaghani Bioorg. Med. Chem. Lett. 16 2006 221
39. I.V. Kozhevnikov Chem. Rev. 98 1998 171
40. T. Okuhara, N. Mizuno, and M. Misono Adv. Catal. 41 1996 113
41. I.V. Kozhevnikov Catalysis for Fine Chemicals, Catalysis by Polyoxometalates Vol. 2 2002 Wiley Chichester Chapter 7
42. M. Misono Chem. Commun. 2001 1141
43. E.F. Kozhevnikova, J. Quartararo, and I.V. Kozhevnikov Appl. Catal., A 245 2003 69
44. H. Firouzabadi, and A.A. Jafari J. Iran. Chem. Soc. 2 2005 85 and references cited therein
45. H. Firouzabadi, N. Iranpoor, and A.A. Jafari Synlett 2005 299
46. J.B. Moffat The Surface and Catalytic Properties of Heteropolyoxometalates 2001 Kluwer New York
47. M.N. Tiofeeva, A.V. Dimidov, and I.V. Kozhevnikov J. Mol. Catal. 79 1993 21
48. R.S. Drago, J.A. Dias, and T. Maier J. Am. Chem. Soc. 119 1997 7702
49. Y. Izumi, K. Urabe, and M. Onaka Zeolite Clay and Heteropoly Acids in Organic Synthesis 1992 Kodansha/VCH Tokyo
50. Typical procedure for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones and -thiones: a mixture containing an appropriate β-dicarbonyl compound (2 mmol), corresponding aldehyde (2 mmol), urea or thiourea (3 mmol) and appropriate amount of catalyst (Table 2) in acetonitrile (5 mL) was stirred rapidly and heated at 80°C in a preheated oil bath for one hour (completion of the reaction was monitored by TLC). The reaction mixture was then filtered to remove the catalyst, and the filtrate was poured into crushed ice. Stirring was continued for several minutes. The solid product was filtered, washed with cold water (2× 30 mL) and recrystallized from ethyl acetate/n-hexane or ethanol to afford pure product. All products were identified by comparing their spectral and physical data with those for authentic samples.
51. T.U. Mayer, T.M. Kapoor, S.J. Haggarty, R.W. King, S.L. Schreiber, and T.J. Mitchison Science 286 1999 971
52. F. Sweet, and J. Fissekis J. Am. Chem. Soc. 95 1973 8741
53. K. Folkers, and T.B. Johnson J. Am. Chem. Soc. 55 1933 3784
54. C.O. Kappe J. Org. Chem. 62 1997 7201
55. C.O. Kappe, and S.F. Falsone Synlett 1998 718