Facile catalyst-free pseudo five-component domino reactions in the expedient synthesis of 5-aroyl-1,3-diarylhexahydropyrimidines

Tetrahedron Letters

Volumn 53, Issue 9, 2012, Pages 1144-1148

  Muthusaravanan, Sivasubramanian ^a   Perumal, Subbu ^a   Almansour, Abdulrahman I ^b  

^a MADURAI KAMARAJ UNIVERSITY   (India)

^b KING SAUD UNIVERSITY   (Saudi Arabia)

Author keywords

(E) 3 (Dimethylamino) 1 arylprop 2 en 1 one; 5 Aroyl 1,3 diarylhexahydropyrimidines; Aniline; Domino reaction; Formaldehyde

Indexed keywords

3 (DIMETHYLAMINO) 1 ARYLPROP 2 EN 1 ONE; 5 AROYL 1,3 DIARYLHEXAHYDROPYRIMIDINE; ANILINE; CARBON; FORMALDEHYDE; NITROGEN; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; CATALYST; CHEMICAL REACTION; DOMINO REACTION; DRUG SYNTHESIS; ELIMINATION REACTION; MANNICH REACTION; MICHAEL ADDITION; POLYMERIZATION;

EID: 84856217393     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.12.097     Document Type: Article

References (67)

1. K.S. Jain, T.S. Chitre, P.B. Miniyar, M.K. Kathiravan, V.S. Bendre, V.S. Veer, S.R. Shahane, and C.J. Shishoo Curr. Sci. 90 2006 793 803
2. T. Suzuki, T. Kubota, and J. Kobayashi Bioorg. Med. Chem. Lett. 21 2011 4220 4223
3. B. Renson, P. Merlin, D. Daloze, J.C. Braekman, Y. Roisin, and J.M. Pasteels Can. J. Chem. 72 1994 105 109
4. A. Guggisberg, K. Drandarov, and M. Hesse Helv. Chim. Acta 83 2000 3035 3042
5. J.C. Braekman, D. Daloze, R. Flammang, and A. Maquestiau Org. Mass Spectrom. 24 1989 837 838
6. K. Drandarov, A. Guggisberg, and M. Hesse Helv. Chim. Acta 82 1999 229 234
7. P.A.S. Smith, and R.N. Loeppky J. Am. Chem. Soc. 89 1967 1147 1157
8. J. Billman, and M. Khan J. Med. Chem. 11 1968 312 314
9. Chang, Y. H.; Evanenga, G. R.; McLamore, W. M. U.S. Patent 3 729 564, 1973; Chem. Abstr. 1974, 79, 18762.
10. B.T. Golding, and I.K. Nassereddin J. Chem. Soc., Perkin Trans. 1 1985 2011 2015
11. R.J. Bergeron, and H.W. Seligsohn Bioorg. Chem. 14 1986 345 355
12. A.Q. Siddiqui, L. Merson-Davies, and P.M. Cullis J. Chem. Soc., Perkin Trans. 1 1999 3243 3252
13. J.A. Bisceglia, M.B. Garcia, R. Massa, M.L. Magri, M. Zani, G.O. Gutkind, and L.R. Orelli J. Heterocycl. Chem. 41 2004 85 90
14. M.S. Khan, and M. Gupta Pharmazie 57 2002 377 383
15. N. Kalyanam, P.C. Parthasarathy, L. Ananthan, S.G. Manyunatha, and M.A. Likhate Indian J. Chem., Sect B 31 1992 243 247
16. P. Vanelle, J. Maldonado, M.P. Crozet, K. Senouki, F. Delmas, M. Gasquet, and P. Timon-David Eur. J. Med. Chem. 26 1991 709 714
17. S. Tu, C. Miao, F. Fang, F. Youjian, T. Li, Q. Zhuang, X. Zhang, S. Zhu, and D. Shi Bioorg. Med. Chem. Lett. 14 2004 1533 1536
18. C.O. Kappe Tetrahedron 49 1993 6937 6963
19. C.O. Kappe Eur. J. Med. Chem. 35 2000 1043 1052
20. D. Russowski, R.F.S. Canto, S.A.A. Sanches, M.G.M. D'Oca, A.D. Fatima, and J.E.D. Carvalho Bioorg. Chem. 34 2006 173 182
21. B. Rodrýguez, and C. Bolm J. Org. Chem 71 2006 2888 2891
22. K. Chantrapromma, J.S. McManis, and B. Ganem Tetrahedron Lett. 21 1980 2475 2476
23. K. Chantrapromma, and B. Ganem Tetrahedron Lett. 22 1981 23 24
24. R.F. Evans Aust. J. Chem. 20 1967 1643 1661
25. H. Finch, E.A. Peterson, and S.A. Ballard J. Am. Chem. Soc. 74 1952 2016 2021
26. C. Jutz, A.F. Kirschner, and R.M. Wagner Chem. Ber. 110 1977 1259 1268
27. I.A. Perillo, M.B. Garcia, J.A. Bisceglia, and L.R. Orelli J. Heterocycl. Chem. 39 2002 655 661
28. A.R. Katrizky, S.K. Singh, and H.Y. He J. Org. Chem. 67 2002 3115 3117
29. M. Mayr, and M.R. Buchmeiser Macromol. Rapid Commun. 25 2004 231 236
30. M. Mayr, K. Wurst, K.H. Ongania, and M.R. Buchmeiser Chem. Eur. J. 10 2004 1256 1266
31. J.E. Díaz, J.Á. Bisceglia, M.C. Mollo, and L.R. Orelli Tetrahedron Lett. 52 2011 1895 1897
32. C. Mukhopadhyay, S. Rana, and R.J. Butcher Tetrahedron Lett. 52 2011 4153 4157
33. H.L. Wei, Z.Y. Yan, Y.N. Niu, G.Q. Li, and Y.M. Liang J. Org. Chem. 72 2007 8600 8603
34. K. Chanda, M.C. Dutta, E. Karim, and J.N. Vishwakarma J. Heterocycl. Chem. 41 2004 627 631
35. For our representative articles see: P. Prasanna, K. Balamurugan, S. Perumal, and J.C. Menéndez Green Chem. 13 2011 2123 2129
36. S. Michael Rajesh, B. Devi Bala, S. Perumal, and J.C. Menéndez Green Chem. 13 2011 3248 3254
37. S. Indumathi, S. Perumal, and J.C. Menéndez J. Org. Chem. 75 2010 472 475
38. For general reviews on multicomponent reactions, see: A. Dömling, and I. Ugi Angew. Chem., Int. Ed. 39 2000 3168 3210
39. A. Ugi Molecules 8 2003 53 66
40. R.V.A. Orru, and M. de Greef Synthesis 10 2003 1471 1499
41. J. Zhu Eur. J. Org. Chem. 2003 1133 1144
42. D. Tejedor, D. González-Cruz, A. Santos-Expósito, J.J. Marrero-Tellado, P. de Armas, and F. García-Tellado Chem. Eur. J. 11 2005 3502 3510
43. D.J. Ramón, and M. Yus Angew. Chem., Int. Ed. 44 2005 1602 1634
44. A. Dömling Chem. Rev. 106 2006 17 89
45. F. Liéby-Muller, C. Simon, T. Constantieux, and J. Rodriguez QSAR Comb. Sci. 25 2006 432 438
46. H. Guo, and J. Ma Angew. Chem., Int. Ed. 45 2006 354 366
47. D. Tejedor, and F. García-Tellado Chem. Soc. Rev 36 2007 484 491
48. G. Guillena, D.J. Ramón, and M. Yus Tetrahedron: Asymmetry 18 2007 693 700
49. B.B. Toure, and D.G. Hall Chem. Rev. 109 2009 4439 4486
50. B. Ganem Acc. Chem. Res. 42 2009 463 472
51. For a monograph on MCRs, see: Zhu, J.; Bienaymé, H. (Eds.), Multicomponent Reactions. Wiley-VCH, 2005.
52. For a symposium in print on MCRs, see: Marek, I. (Ed.) Tetrahedron Symposia-in-Print 2005, 67, 11299.
53. For reviews on the use of MCRs in drug discovery, see: L.F. Tietze, and A. Modi Med. Res. Rev. 20 2000 304 322
54. L. Weber Curr. Med. Chem. 9 2002 2085 2093
55. C. Hulme, and V. Gore Curr. Med. Chem. 10 2003 51 80
56. For reviews, see: J. Sapi, and J.Y. Laronze Arkivoc 2004 208 222
57. N. Isambert, and R. Lavilla Chem. Eur. J. 14 2008 8444 8454
58. J.D. Sunderhaus, and S.F. Martin Chem. Eur. J. 15 2009 1300 1308
59. S.B. Ferreira, D.R. da Rocha, J.W.M. Carneiro, W.C. Santos, and V.F. Ferreira Synlett 11 2011 1551 1554
60. G. Musumarra, and C. Sergi Heterocycles 37 1994 1033 1039
61. S.-C. Lee, and S.B. Park Chem. Commun. 36 2007 3714 3716
62. R. Leuckart Ber. Dtsch. Chem. Ges. 18 1885 2341 2344
63. O. Wallach Ber. Dtsch. Chem. Ges. 24 1891 3992 3993
64. M.L. Moore Org. React. 5 1949 301 330
65. O. Wallach Ann. 272 1892 99
66. V.M. Muzalevskiy, G.N. Valentine, A.V. Shastin, E.S. Balenkova, and G. Haufe J. Fluorine Chem. 129 2008 1052 1055
67. D. O'Connor, A. Lauria, S.P. Bondi, and S. Saba Tetrahedron Lett. 52 2011 129 132