Zirconium oxide (NP) - Ionic liquid as an efficient media for the domino Knoevenagel hetero Diels-Alder reaction with unactivated alkynes

Comptes Rendus Chimie

Volumn 15, Issue 4, 2012, Pages 283-289

  Balalaie, Saeed ^a   Poursaeed, Ali ^a   Khoshkholgh, Malihe Javan ^a   Bijanzadeh, Hamid Reza ^b   Wolf, Eckardt ^c  

^a K N TOOSI UNIVERSITY OF TECHNOLOGY   (Iran)

^b TARBIAT MODARES UNIVERSITY   (Iran)

^c Tofigh Daru Res and Eng Co   (Iran)

Author keywords

bmim NO 3 ; Domino Knoevenagel hetero Diels Alder reaction; Ionic liquid in synthesis of heterocycles; Unactivated alkynes; ZrO 2 nanopowder (ZrO 2 NP)

Indexed keywords

EID: 84859106213     PISSN: 16310748     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.crci.2011.12.002     Document Type: Article

References (68)

1. L.F. Tietze, and F. Hauner M. Shibasaki, J.F. Stoddart, Stimulating concepts in chemistry 2000 John Wiely-VCH Weinheim 39 64
2. L.F. Tietze, G. Brasche, and K.M. Gericke Domino reactions in organic synthesis 2006 Wiley-VCH
3. C.J. Chapman, and C.G. Frost Synthesis 2007 1
4. D. Enders, C. Grondal, and M.R.M. Hüttl Angew. Chem. Int. Ed. 46 2007 1570
5. L.F. Tietze Chem. Rev. 96 1996 115
6. L.F. Tietze, and N. Rackelmann J. Zhu, H. Bienayme, Multicomponent reactions 2005 Wiley-VCH Weinheim 121 167
7. L.F. Tietze, and N. Rackelmann Pure Appl. Chem. 76 2004 1967
8. L.F. Tietze J. Heterocycl. Chem. 27 1990 47
9. L.F. Tietze, N. Rackelmann, and I. Müller Chem. Eur. J. 10 2004 2722
10. M.D. Burke, and S.L. Schreiber Angew. Chem. Int. Ed. 43 2004 46
11. N. Isambert, and R. Lavilla Chem. Eur. J. 14 2008 8444
12. B.A. Arndtsen Chem. Eur. J. 15 2009 302
13. J.D. Sunderhaus, and S.F. Martin Chem. Eur. J. 15 2009 1300
14. M. Leibeling, D.C. Koester, M. Pawliczek, S.C. Schild, and D.B. Werz Nature Chem. Bio. 6 2010 199
15. M. Leibeling, B. Milde, D. Kratzert, D. Stalke, and D.B. Werz Chem. Eur. J. 47 2011 9888
16. Y. Yammamoto J. Org. Chem. 72 2007 7817 and references cited therein
17. V. Gouverneur, and M. Reiter Chem. Eur. J. 11 2005 5806
18. A. Fürstner, and C.C. Stimson Angew. Chem. Int. Ed. 46 2007 8845
19. K.C. Majumdar, A. Taher, and S. Ponra Synthesis 5 2010
20. K.C. Majumdar, A. Taher, and S. Ponra Tetrahderon Lett. 51 2010 147
21. M. Kiamehr, and F.M. Moghaddam Tetrahedron Lett. 50 2009 6723
22. F.M. Moghaddam, M. Kiamehr, S. Taheri, and Z. Mirjafary Helv. Chim. Acta 93 2010 964
23. A.O. Bryhas, Y.I. Horak, Y.V. Ostapiuk, M.D. Obushak, and V.S. Matiychuk Tetrahedron Lett. 52 2011 2324
24. Y. Liu, F. Song, Z. Song, M. Liu, and B. Yan Org. Lett. 7 2005 5409
25. C. Bruneau Angew. Chem. Int. Ed. 44 2005 2328
26. N. Asao, K. Sato, and Y. Yamamoto J. Org. Chem. 70 2005 3682
27. N. Asao, K. Takashi, S. Lee, T. Kasahara, and Y. Yamamoto J. Am. Chem. Soc. 124 2002 12650
28. T. Shibata, Y. Ueno, and K. Kanda Synlett 2006 411
29. N. Asao, S. Yudha, T. Nogami, and Y. Yamamoto Angew. Chem. Int. Ed. 44 2005 5526
30. C.S. Yi, and S.Y. Yun J. Am. Chem. Soc. 127 2005 1700
31. D.S. Ermolat'ev, V.P. Mehta, and E.V. Eycken Synlett 2007 3117
32. T. Godet, C. Vaxelaie, C. Michel, A. Milet, and P. Belmont Chem. Eur. J. 13 2007 5632
33. Y. Xiao, and J. Zhang Angew. Chem. Int. Ed. 47 2008 1903
34. O. Leogane, and H. Lebel Angew. Chem. Int. Ed. 47 2008 350
35. N. Asao, T. Kasahara, and Y. Yamamoto Angew. Chem. Int. Ed. 42 2003 3504
36. N.T. Patil, H. Wu, and Y. Yamamoto J. Org. Chem. 70 2005 4531
37. P. Bertrand, and J.P. Gesson J. Org. Chem. 72 2007 3596
38. N.T. Patil, and Y. Yamamoto J. Org. Chem. 69 2004 5139
39. C. Chen, and P.G. Dormer J. Org. Chem. 70 2005 6964
40. W. Zhu, and D. Ma Chem. Commun. 2004 888
41. G. Evindar, and R. Batey J. Org. Chem. 71 2006 1802
42. B. Sreedhar, P.S. Reddy, and N.S. Kumar Tetrahedron Lett. 47 2006 3055
43. T. Jin, S. Kamijo, and Y. Yamamoto Eur. J. Org. Chem. 2004 3789
44. M.J. Khoshkholgh, S. Balalaie, R. Gleiter, and F. Rominger Tetrahedron 64 2008 10924
45. M.J. Khoshkholgh, S. Balalaie, H.R. Bijanzadeh, F. Rominger, and J.H. Gross Tetrahedron Lett. 49 2008 6965
46. M.J. Khoshkholgh, S. Balalaie, H.R. Bijanzadeh, and J.H. Gross Arkivocix 2009 114
47. M.J. Khoshkholgh, S. Balalaie, H.R. Bijanzadeh, and J.H. Gross Synlett 2009 55
48. M. Mollazadeh, M.J. Khoshkholgh, S. Balalaie, F. Rominger, and H.R. Bijanzadeh J. Heterocycl. Chem. 47 2010 1200
49. M.J. Khoshkholgh, M. Lotfi, S. Balalaie, and F. Rominger Tetrahedron 65 2009 4228
50. L. Chen, Y. Liu, and Y. Li J. Alloys Compounds 381 2004 266
51. G. Li, W. Li, M. Zhang, and K. Tao Appl. Catalysis A 273 2004 233
52. E.I. Ross-Medgaarden, W.V. Knowles, T. Kim, M.S. Wong, W. Zhou, C.J. Kiely, and I.E. Wachs J. Catal. 256 2008 108
53. M. Freemantle An introduction to ionic liquids 2010 RSC Publishing Cambridge
54. N.V. Plechkova, and K.R. Seddon Chem. Soc. Rev. 37 2008 123 and references cited therein
55. H. Zhao Chem. Eng. Commun. 193 2006 1660
56. N. Isambert, M.D.M. Sanchez Duque, J.C. Plaquevent, Y. Génisson, J. Rodriguez, and T. Constantieux Chem. Soc. Rev. 40 2011 1347
57. V.I. Parvulescu, and C. Hardacre Chem. Rev. 107 2007 2615
58. T. Welton Chem. Rev. 99 1999 2071
59. P. Wasserscheid, and W. Keim Angew. Chem. Int. Ed. 39 2000 3773
60. J.S. Wilkes Green Chem. 4 2002 73
61. D.G. Gu, S.J. Ji, Z.Q. Jiang, M.F. Zhou, and T.P. Loh Synlett 2005 959
62. J.R. Harjani, S.J. Nara, and M.M. Salunkhe Tetrahedron Lett. 43 2002 1127
63. T. Akaiyama, A. Suzuki, and K. Fuchibe Synlett 2005 1024
64. B.C. Ranu, S. Banerjee, and A. Das Tetrahedron Lett. 47 2006 881
65. B.C. Ranu, and S. Banerjee Org. Lett. 7 2005 3049
66. B.C. Ranu, and R. Jana Eur. J. Org. Chem. 2006 3767
67. B.C. Ranu, S. Banerjee, and R. Jana Tetrahedron 63 2007 776
68. J.M. Xu, C. Qian, B.K. Liu, Q. Wu, and X.F. Lin Tetrahedron 63 2007 986