ZrCl4 or ZrOCl2 under neat conditions: optimized green alternatives for the Biginelli reaction

Tetrahedron Letters

Volumn 48, Issue 33, 2007, Pages 5777-5780

  Rodríguez Domínguez, Juan Carlos ^a   Bernardi, Dan ^a   Kirsch, Gilbert ^a  

^a FR CNRS 2843   (France)

Author keywords

Biginelli reaction; Neat conditions; Zirconia catalysts

Indexed keywords

3,4 DIHYDROPYRIMIDIN 2(1H) ONE; ALDEHYDE; CHLORIDE; DIAMIDE; DIKETONE; LEWIS ACID; N,N DIMETHYLFORMAMIDE; PYRIMIDINONE DERIVATIVE; THIOUREA; THIOXO 3,4 DIHYDROPYRIMIDIN 2(1H) ONE; UNCLASSIFIED DRUG; YTTERBIUM; ZIRCONIUM OXIDE;

ARTICLE; BIGINELLI REACTION; CATALYST; CHEMICAL STRUCTURE; POLYMERIZATION; REACTION TIME; REPRODUCIBILITY;

EID: 34447507813     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.06.104     Document Type: Article

References (56)

1. Biginelli P. Gazz. Chim. Ital. 23 (1893) 360-413
2. Kappe C.O. Tetrahedron 49 (1993) 6937-6963
3. Kappe C.O. Acc. Chem. Res. 33 (2000) 879-888
4. Atwal K.S., Swanson B.N., Unger S.E., Floyd D.M., Moreland S., Hedberg A., and O'Reilly B.C. J. Med. Chem. 34 (1991) 806-811
5. Kappe C.O. Eur. J. Med. Chem. 35 (2000) 1043-1052
6. Mokrosz J.L., Paluchowska M.H., Szneler E., and Drozdz B. Arch. Pharm. (Weinheim, Germany) 322 (1989) 231-235
7. Abelman M.M., Smith S.C., and James D.R. Tetrahedron Lett. 44 (2003) 4559-4562
8. Yarim M., Sarac S., Kilic F.S., and Erol K. Il Farmaco 58 (2003) 17-24
9. Byk G., Gettlieb H.E., Herscovici J., and Mirkin F. J. Comb. Chem. 2 (2000) 732-735
10. Folkers K., and Johnson T.B. J. Am. Chem. Soc. 55 (1933) 2886-2893
11. Folkers K., and Johnson T.B. J. Am. Chem. Soc. 55 (1933) 3784-3791
12. Hu E.H., Sidler D.R., and Dolling U.H. J. Org. Chem. 63 (1998) 3454-3457
13. Lu J., Bai Y., Wang Z., Yang B., and Ma H. Tetrahedron Lett. 41 (2000) 9075-9078
14. Bose D.S., Fatima L., and Mereyala H.B. J. Org. Chem. 68 (2003) 587-590
15. Ranu B.C., Hajra A., and Jana U. J. Org. Chem. 65 (2000) 6270-6272
16. Rafiee E., and Jafari H. Bioorg. Med. Chem. Lett. 16 (2006) 2463-2466
17. Ramalinga K., Vijayalakshmi P., and Kaimala T.N.B. Synlett (2001) 863-865
18. Paraskar A.S., Dewkar G.K., and Sudalai A. Tetrahedron Lett. 44 (2003) 3305-3308
19. Zhu Y.L., Huang S.L., and Pan Y.J. Eur. J. Org. Chem. (2005) 2354-2367
20. Yadav J.S., Reddy B.V.S., Srinivas R., Venugopal C., and Ramalingam T. Synthesis 9 (2001) 1341-1345
21. Maiti G., Kundua P., and Guin C. Tetrahedron Lett. 44 (2003) 2757-2758
22. Fu N.Y., Yuan Y.F., Cao Z., Wang S.W., Wang J.T., and Peppe C. Tetrahedron 58 (2002) 4801-4807
23. Lu J., and Ma H. Synlett (2000) 63-64
24. Sabitha G., Reddy G.S.K.K., Reddy Ch.S., and Yadav J.S. Synlett (2003) 858-860
25. Ma Y., Qian C., Wang L., and Yang M. J. Org. Chem. 65 (2000) 3864-3868
26. Dondoni A., and Massi A. Tetrahedron Lett. 42 (2001) 7975-7978
27. Yuki T., Hashimoto M., Nishiyama Y., and Ishii Y. J. Org. Chem. 58 (1993) 4497-4499
28. Das B., Ravikanth B., Reddy K.R., and Rao B.V. Helv. Chim. Acta 90 (2007) 105-109
29. Rodríguez-Domínguez J.C., and Kirsch G. Synthesis 11 (2006) 1895-1897
30. Nagawade R.R., and Shinde D.B. Russ. J. Org. Chem. 42 (2006) 453-454
31. Mantri K., Komura K., and Sugi Y. Synthesis 12 (2005) 1939-1944
32. Sharma G.V.M., Reddy J.J., Lakshmi P.S., and Krishna P.R. Tetrahedron Lett. 46 (2005) 6119-6121
33. Firouzabadi H., Iranpoor N., and Karimi B. Synlett (1999) 319-320
34. Firouzabadi H., Iranpoor N., and Karimi B. Synlett (1999) 321-323
35. Reddy C.V., Mahesh M., Raju P.V.K., Babu T.R., and Reddy V.V.N. Tetrahedron Lett. 43 (2002) 2657-2659
36. Shirini F., Zolfigol M.A., and Mollarazi E. Synth. Commun. 36 (2006) 2307-2310
37. 6): δ 194.81, 174.07, 144.72, 140.19, 132.41, 132.23, 128.55, 127.89, 127.45, 126.35, 126.13, 124.98, 124.91, 110.18, 54.03, 30.39, 18.29. Elem. Anal. Calcd: C, 68.89; H, 5.44; N, 9.45; O, 5.40; S, 10.82. Found: C, 68.92; H, 5.40; N, 9.48; O, 5.35; S, 10.85.
38. 6): δ 174.23, 164.13, 146.72, 146.62, 141.64, 138.96, 133.63, 131.47, 129.20, 128.32, 127.80, 124.36, 124.27, 99.86, 59.51, 52.45, 13.19. Elem. Anal. Calcd: C, 54.61; H, 3.86; Cl, 8.48; N, 10.06; O, 15.32; S, 7.67. Found: C, 54.64; H, 3.83; Cl, 8.50; N, 10.09; O, 15.29; S, 7.65.
39. Foroughifar N., Mobinikhaledi A., Jirandehi H.F., and Memar S. Phosphorus, Sulfur Silicon Relat. Elem. 178 (2003) 1269-1276
40. Putilova E.S., Kryshtal G.V., Zhdankina G.M., Troitskii N.A., and Zlotin S.G. Russ. J. Org. Chem. 41 (2005) 512-516
41. Putilova E.S., Kryshtal G.V., Zhdankina G.M., Troitskii N.A., and Zlotin S.G. Zh. Org. Khim. 41 (2005) 524-528
42. Sabitha G., Reddy G.S.K.K., Reddy K.B., and Yadav J.S. Tetrahedron Lett. 44 (2003) 6497-6499
43. Wang L., Qian C., Tian H., and Ma Y. Synth. Commun. 33 (2003) 1459-1468
44. Gartner M., Sunder-Plassmann N., Seiler J., Utz M., Vernos I., Surrey T., and Giannis A. Chem. Bio. Chem. 6 (2005) 1173-1177
45. Yadav J.S., Reddy B.V.S., Sridhar P., Reddy J.S.S., Nagaiah K., Lingaiah N., and Saiprasad P.S. Eur. J. Org. Chem. 3 (2004) 552-557
46. Pal R., Handa R.N., and Pujari H.K. Indian J. Chem., Sect. B 33 (1994) 629-633
47. Sweet F., and Fissekis J.D. J. Am. Chem. Soc. 95 (1973) 8741-8749
48. Mobinikhaledi A., Forughifar N., and Goodarzi F. Phosphorus, Sulfur, Silicon Relat. Elem. 178 (2003) 2539-2544
49. Mobinikhaledi A., Forughifar N., and Ahmadi B. Phosphorus, Sulfur, Silicon Relat. Elem. 180 (2005) 339-345
50. Mobinikhaledi A., Forughifar N., and Ghorbani A.N. Phosphorus, Sulfur, Silicon Relat. Elem. 180 (2005) 1713-1719
51. Fu N.Y., Yuan Y.F., Cao Z., Wang S.W., Wang J.T., and Peppe C. Tetrahedron 58 (2002) 4801-4807
52. Shanmugam P., Annie G., and Perumal P.T. J. Het. Chem. 40 (2003) 879-884
53. Rana K., Kaur B., and Kumar B. Indian J. Chem., Sect. B 43 (2004) 1553-1557
54. Yarim M., Sarac S., Ertan M., Batu O., and Erol K. Il Farmaco 54 (1999) 359-363
55. Sherif S.M., Youssef M.M., Mobarak K.M., and Abdel-Fattah A.-S.M. Tetrahedron 49 (1993) 9561-9572
56. Bózsing D., Sahér P., Gigler G., and Kovács G. Eur. J. Med. Chem. 31 (1996) 663-668