One-pot synthesis of dihydropyrimidinones using facile and reusable polyoxometalate catalysts for the Biginelli reaction

Applied Catalysis A: General

Volumn 309, Issue 1, 2006, Pages 44-51

  Fazaeli, Razieh ^a   Tangestaninejad, Shahram ^a   Aliyan, Hamid ^b   Moghadam, Majid ^c  

^a UNIVERSITY OF ISFAHAN   (Iran)

^b ISLAMIC AZAD UNIVERSITY   (Iran)

^c YASOUJ UNIVERSITY   (Iran)

Author keywords

Biginelli reaction; Environmentally friendly processes; Heterogeneous; Homogeneous; Multicomponent reactions (MCR); Polyoxometalates (POMs)

Indexed keywords

ALDEHYDES; CATALYST ACTIVITY; CATALYSTS; POLYCONDENSATION; REACTION KINETICS; SYNTHESIS (CHEMICAL);

BIGINELLI REACTION; ENVIRONMENTALLY FRIENDLY PROCESSES; HETEROGENEOUS; HOMOGENEOUS; MULTICOMPONENT REACTIONS (MCR); POLYOXOMETALATES (POM);

KETONES;

EID: 33745231667     PISSN: 0926860X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.apcata.2006.04.043     Document Type: Article

References (68)

1. Biginelli P.G. Chim. Ital. 23 (1893) 360
2. Cho H., Ueda M., Shima K., Mizuno A., Hayashimatsu M., Ohnaka Y., Takeuchi Y., Hamaguchi M., Aisaka K., Hidaka T., Kawai M., Takeda M., Ishihara T., Funahashi K., Satah F., Morita M., and Noguchi T.J. Med. Chem. 32 (1989) 2399
3. Atwal K.S., Rovnyak G.C., Kimball S.D., Floyd D.M., Moreland S., Swanson B.N., Gougoutas J.Z., Schwartz J., Smillie K.M., and Malley M.F.J. Med. Chem. 33 (1990) 2629
4. Rovnyak G.C., Kimball S.D., Beyer B., Cucinotta G., Dimarco J.D., Gougoutas J., Hedberg A.O., Malley M., McCarthy J.P., Zhang R., and Moreland S. J. Med. Chem. 38 (1995) 119
5. Atwal K.S., Swanson B.N., Unger S.E., Floyd D.M., Moreland S., Hedberg A.O., and Reilly B.C. J. Med. Chem. 34 (1991) 806
6. Grover G.J., Dzwonczyk S., McMullen D.M., Normadinam C.S., Sleph P.G., and Moreland S.J. J. Cardiovasc. Pharmacol. 26 (1995) 289
7. Kappe C.O. J. Org. Chem. 62 (1997) 7201
8. Folkers K., Harwood H.J., and Johnson T.B. J. Am. Chem. Soc. 54 (1932) 3751
9. Folkers K., and Johnson T.B. J. Am. Chem. Soc. 55 (1933) 2886
10. Zavyalov S.I., and Kulikova L.B. Khim. Farm. Zh. 126 (1992) 116
11. Gupta R., Gupta A.K., Paul S., and Kachroo P.L. Ind. J. Chem. 34B (1995) 151
12. Hu E.H., Sidler D.R., Dolling U.H., and Patane M.A. PCT Int. Appl. WO. 9,721,687; Chem. Abstr. 127 (1997) 121750v
13. O'Reilly B.C., and Atwal K.S. Heterocycles 26 (1987) 1185
14. Shutalev A.D., and Kuksa V.A. Khim. Geterotsikl. Soedin. (1997) 105
15. Shutalev A.D., Kishko E.A., Sivova N., and Kuzenetsov A.Y. Molecules 3 (1998) 100
16. Wipf P., and Cunningham A. Tetrahedron Lett. 36 (1995) 7819
17. Studer A., Jeser P., Wipf P., and Curran D.P. J. Org. Chem. 62 (1997) 2917
18. Hu E.H., Sidler D.R., and Dolling U.H. J. Org. Chem. 63 (1998) 3454
19. Ranu B.C., Hajra A., and Jana U.J. Org. Chem. 65 (2000) 6270
20. Yadav J.S., Reddy B.V.S., Naidu J.J., and Sadashiv K. Chem. Lett. 33 7 (2004) 926
21. Gangadasu B., Palaniappan S., and Jayathirtha Rao V. Synlett 7 (2004) 1285
22. Russowsky D., Lopes F.A., Silva V.S.S., Canto K.F.S., Montes D'Oca M.G., and Godoi M.N. J. Braz. Chem. Soc. (2004) 165
23. Narsaiah A.V., and Nagaiah B.K. Synthesis 8 (2004) 1253
24. Hazarkhani H., and Karimi B. Synthesis 8 (2004) 1239
25. Dondoni A., and Massi A. Tetrahedron Lett. 42 (2001) 7975
26. Falsone F.S., and Kappe O. Arkivoc ii (2001) 122
27. Kumar K.A., Kasthuraiah M., Reddy C.S., and Reddy D. Tetrahedron Lett. 42 (2001) 7873
28. Yadav J.S., Subba Reddy B.V., Srinivas R., Venugopal C., and Ramalingam T. Synthesis (2001) 1341
29. Ramalinga K., Vijayalakshmi P., and Kaimal T.N.B. Synlett (2001) 863
30. Reddy C.V., Mahesh M., Raju P.V.K., Babu R., and Reddy V.V.N. Tetrahedron Lett. 43 (2002) 2657
31. Ma Y., Qian C., Wang L., and Yang M. J. Org. Chem. 65 (2000) 3864
32. Lu J., and Bai Y. Synthesis (2002) 466
33. Peng J., and Deng Y. Tetrahedron Lett. 42 (2001) 5917
34. Varala R., Alam M.M., and Adapa S.R. Synlett 1 (2003) 67
35. Mitra A.K., and Banerjee K. Synlett 10 (2003) 1509
36. Rani V.R., Srinivas N., Kishan M.R., Kulkarni S.J., and Raghavan K.V. Green Chem. 3 (2001) 305
37. 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. (2004) 552
38. De S.K., and Gibbs R.A. Synthesis 11 (2005) 1748
39. Cepanec I., Litvic M., Bartolincic A., and Lovric M. Tetrahedron 61 (2005) 4275
40. Zhang G.L., and Cai H.X. Synth. Commun. 35 (2005) 829
41. Saxena I., Borah D.C., and Sarma J.C. Tetrahedron Lett. 46 (2005) 1159
42. Zhu Y.L., Pan Y.J., and Huang S.L. Synth. Commun. 34 (2004) 3167
43. Chari M.A., and Syamasundar K.J. Mol. Catal. A: Chem. 221 (2004) 137
44. Jin T.S., Wang H.X., Xing C.Y., Li X.L., and Li T.S. Synth. Commun. 34 16 (2004) 3009
45. Turchi C.S., and Ollis D.F. J. Catal. 122 (1990) 178
46. Okura T., Mizuno N., and Misono M. Adv. Catal. 41 (1996) 113
47. Mizuno N., and Misono M. J. Mol. Catal. A: Chem. 86 (1994) 319 (special issue)
48. Mizuno N., and Misono M. Chem. Rev. 98 (1998) 199
49. Khenkin A.M., and Neumann R. J. Am. Chem. Soc. 123 (2001) 6437-6438
50. Khenkin A.M., and Neumann R. J. Am. Chem. Soc. 124 (2002) 4198-4199
51. Firouzabadi H., Iranpoor N., and Amani K. Synthesis 1 (2002) 59-62
52. Yamada Y.M.A., Tabata H., Takahashi H., and Ikegami S. Synlett 12 (2002) 2031-2034
53. Yamada Y.M.A., Ichinohe M., Takahashi H., and Ikegami S. Org. Lett. 3 12 (2001) 1837-1840
54. da Silva K.A., Robles-Dutenhefner P.A., Sousa E.M.B., Kozhevnikova E.F., Kozhevnikov I.V., and Gusevskay E.V. Catal. Commun. 5 (2004) 425-429
55. Kaur J., Griffin K., Harrison B., and Kozhevnikov I.V. J. Catal. 208 (2002) 448-455
56. Castro C., Corma A., and Primo J. J. Mol. Catal. A: Chem. 177 (2002) 273-280
57. Kozhevnikova E.F., Rafiee E., and Kozhevnikov I.V. Appl. Catal. A: Chem. 260 (2004) 25-34
58. Liu Y., Su Kim S., and Pinnavaia T.J. J. Catal. 225 (2004) 381-387
59. Hori H., Hayakawa E., Koike K., Einaga H., and Ibusuki T. J. Mol. Catal. A: Chem. 211 (2004) 35-41
60. De Castro C., Primo J., and Corma A. J. Mol. Catal. A: Chem. 134 (1998) 215-222
61. Shikata S., Okuhara T., and Misono M. J. Mol. Catal. A: Chem. 100 (1995) 49-59
62. Kozhevnikov I.V. Catalysis by Polyoxometalates (2002), Wiley, England
63. Chang T.H. J. Chem. Soc. Faraday Trans 91 2 (1995) 375
64. Misono M., Misono N., Katamura K., Kasai A., Konishi Y., Sakata K., Okuhara T., and Yoneda Y. Bull. Chem. Soc. Jpn. 55 (1982) 400
65. Fournier M., Thouvenot R., and Rocchiccioli-Deltcheff C. J. Chem. Soc. Faraday Trans. 87 2 (1991) 349
66. Yadav G.D., and Kirthivasan N. J. Chem. Soc. Faraday Trans. (1995) 203
67. Lee K.W., Mizuno N., Okuhara T., and Misono M. Bull. Chem. Soc. Jpn. 62 (1998) 1731
68. Southward B.W.L., Vaughan J.S., and Connor C.T.O. J. Catal. 153 (1995) 293