TaBr5-catalyzed Biginelli reaction: one-pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones/thiones under solvent-free conditions

Tetrahedron Letters

Volumn 48, Issue 31, 2007, Pages 5407-5409

  Ahmed, Naseem ^a   van Lier, Johan E ^a  

^a UNIVERSITY OF SHERBROOKE   (Canada)

Author keywords

3,4 Dihydropyrimidin 2 (1H) ones thiones; Solvent free conditions; TaBr5 catalyzed Biginelli reaction

Indexed keywords

3,4 DIHYROPYRIMIDIN 2(1H) ONE DERIVATIVE; BROMIDE; PYRIMIDINONE DERIVATIVE; TANTALUM; TANTALUM BROMIDE; UNCLASSIFIED DRUG;

ARTICLE; BIGINELLI REACTION; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ONE POT SYNTHESIS; ROOM TEMPERATURE;

EID: 34347366185     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.06.005     Document Type: Article

References (53)

1. Ugi I., Domling A., and Horl W. Endeavour 18 (1994) 115-122
2. Tietze L.F., and Lieb M.E. Curr. Opin. Chem. Biol. 2 (1998) 363-371
3. Mabry J., and Ganem B. Tetrahedron Lett. 47 (2006) 55-56
4. Ramon D.J., and Yus M. Angew. Chem., Int. Ed. 44 (2005) 1602-1634
5. Kappe C.O. Acc. Chem. Res. 33 (2000) 879-888
6. Kappe C.O. Eur. J. Med. Chem. 35 (2000) 1043-1052
7. Biginelli P. Gazz. Chim. Ital. 23 (1893) 360-413
8. Sanjeev P., and Gokavi G.S. Catal. Commun. 8 (2007) 279-284
9. Russowsky D., Canto R.F.S., Sanches S.A.A., D'Oca M.G.M., Fatima A.D., and Carvalho J.E.D. Bioorg. Chem. 34 (2006) 173-182
10. Kappe C.O. Tetrahedron 49 (1993) 6937-6963
11. Rovnyak G.C., Atwal K.S., Hedberg A., Kimball S.D., Moreland S., Gougoutas J.Z., O'Reilly B.C., Schwartz J., and Malley M.F. J. Med. Chem. 35 (1992) 3254-3263
12. Grover G.J., Dzwonczyk S., McMullen D.M., Normandin D.E., Parham C.S., Sleph P.G., and Moreland S. J. Cardiovasc. Pharmacol. 26 (1995) 289-294
13. Nagarathnam D., Miao S.W., Lagu B., Harrell M.C., Vyas K.P., and Gluchowski C. J. Med. Chem. 42 (1999) 4764-4777
14. Barrow J.C., Nantermet P.G., Nagarathnam D., and Forray C. J. Med. Chem. 43 (2000) 2703-2718
15. Gartner M., Sunder-Plassmann N., Seiler J., Utz M., Vernos I., Surrey T., and Giannis A. ChemBioChem 6 (2005) 1173-1177
16. Mayer T.U., Kapoor T.M., Mitchison T.J., and Schreiber S. Chem. Biol. 7 (2000) 275-286
17. Manhas M.S., Ganguly S.N., Mukherjee S., Jain A.K., and Bose A.K. Tetrahedron Lett. 47 (2006) 2423-2425
18. Wang J.-S., Li J.-T., and Lin Z.-P. Letts. Org. Chem. 3 (2006) 523-525
19. Dandia A., Saha M., and Taneja H. J. Fluorine Chem. 90 (1998) 17-21
20. Liu C., Wang J., and Li Y. J. Mol. Catal. A: Chem. 258 (2006) 367-370
21. Kapoor K.K., Ganai B.A., Kumar S., and Andotra C.S. Can. J. Chem. 84 (2006) 433-437
22. Li W., and Lam Y. J. Comb. Chem. 7 (2005) 721-725
23. Legeay J.C., Eynde J.J.V., and Bazureau J.P. Tetrahedron Lett. 48 (2007) 1063-1068
24. Desai B., Dallinger D., and Kappe C.O. Tetrahedron 62 (2006) 4651-4664
25. Hassani Z., Islami M.R., and Kalantari M. Bioorg. Med. Chem. Lett. 16 (2006) 4479-4482
26. Hanane E.B., Fathallaah B., Samira S., Said B., Hassan B.L., and Said S. Letts. Org. Chem. 2 (2005) 561-565
27. Fu N.Y., Yuan Y.F., Cao Z., Wang S.W., Wang J.T., and Peppe C. Tetrahedron 58 (2002) 4801-4807
28. Kalita H.R., and Phukan P. Catal. Commun. 8 (2007) 179-182
29. Bhosale R.S., Bhosale S.V., Bhosale S.V., Wang T., and Zubaidha P.K. Tetrahedron Lett. 45 (2004) 9111-9113
30. Sabitha G., Reddy G.S.K.K., Reddy C.S., and Yadav J.S. Synlett (2003) 858-860
31. Ma Y., Qian C., Wang L., and Yang M. J. Org. Chem. 65 (2000) 3864-3868
32. Suzuki I., Suzumura Y., and Takeda K. Tetrahedron Lett. 47 (2006) 7861-7864
33. Adib M., Ghanbary K., Mostofi M., and Ganjali M.R. Molecules 11 (2006) 649-654
34. Bose D.S., Fatima L., and Mereyala H.B. J. Org. Chem. 68 (2003) 587-590
35. De S.K., and Gibbs R.A. Synthesis (2005) 1748-1750
36. Reddy C.V., Mahesh M., Raju P.V.K., Babu T.R., and Reddy V.V.N. Tetrahedron Lett. 43 (2002) 2657-2659
37. Maiti G., Kundu P., and Guin C. Tetrahedron Lett. 44 (2003) 2757-2758
38. Pasha M.A., and Puttaramegowda J.V. Heterocycl. Commun. 12 (2006) 61-66
39. Debache A., Boumoud B., Amimour M., Belfaitah A., Rhouati S., and Carboni B. Tetrahedron Lett. 47 (2006) 5697-5699
40. Bose A.K., Manhas M.S., Pednekar S., Dang H., He W., and Mandadi A. Tetrahedron Lett. 46 (2005) 1901-1903
41. Yadav J.S., Reddy B.V.S., Lingaiah N., and Saiprasad P.S. Eur. J. Org. Chem. (2004) 552-557
42. Tu S., Fang F., Shi D., and Wang X. Tetrahedron Lett. 44 (2003) 6153-6155
43. Chen W.-Y., Qin S., and Jin J.R. Catal. Commun. 8 (2007) 123-126
44. Chen X.-H., Xu X.-Y., Liu H., Cun L.-F., and Gong L.-Z. J. Am. Chem. Soc. 128 (2006) 14802-14803
45. Shaabani A., Bazgir A., and Teimouri F. Tetrahedron Lett. 44 (2003) 857-859
46. Amini M.M., Shaabani A., and Bazgir A. Catal. Commun. 7 (2006) 843-847
47. Kumar B., Kaur B., Kaur J., Parmar A., Anand R.D., and Kumar H. Indian J. Chem. 41B (2002) 1526-1530
48. Ahmed N., and van Lier J.E. Tetrahedron Lett. 47 (2006) 2725-2729
49. Ahmed N., and van Lier J.E. Tetrahedron Lett. 48 (2007) 13-15
50. Ahmed N., and van Lier J.E. Tetrahedron Lett. 47 (2006) 5345-5349
51. Ahmed N., and Ansari W.H. J. Chem. Res. (S) 9 (2003) 572-573
52. Ahmed N., Ali H., and van Lier J.E. Tetrahedron Lett. 46 (2005) 253-256
53. 5. The solvent was gradually evaporated by heating and the neat reaction mixture was heated with stirring for 40-45 min at 70-80 °C. Product precipitation started after 15 min, TLC monitoring showed that the reaction was completed after 45 min. After cooling the solid precipitate was filtered and washed with cold water and ethanol under reduced pressure and the residue was crystallized from ethanol or ethyl acetate-hexane (1:3) to afford the pure product (4).