An efficient and rapid intramolecular aza-Michael addition of 2′-aminochalcones using ionic liquids as recyclable reaction media

Tetrahedron Letters

Volumn 53, Issue 32, 2012, Pages 4059-4061

  Chelghoum, M ^a   Bahnous, M ^a   Bouraiou, A ^a   Bouacida, S ^a   Belfaitah, A ^a  

^a Universite Mentouri Constantine   (Algeria)

Author keywords

2 Aminochalcone; Dihydroquinolin 4(1H) one; Hetero Michael reaction; Ionic liquid

Indexed keywords

1 BUTYL 3 METHYLIMIDAZOLIUM TETRAFLUOROBORATE; CHALCONE DERIVATIVE; IONIC LIQUID; SOLVENT;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; CYCLIZATION; DRUG SYNTHESIS; ISOMERIZATION; MICHAEL ADDITION; REACTION TIME;

EID: 84863613979     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.05.097     Document Type: Article

References (61)

1. P. Hradil, J. Hlavac, M. Soural, M. Hajduch, M. Kolar, and R. Vecerova Mini-Rev. Med. Chem. 9 2009 696
2. R.D. Larsen D.S. Black, Science of Synthesis Vol. 15 2005 Thieme Stuttgart 551
3. Y. Xia, Z.-Y. Yang, P. Xia, K.F. Bastow, Y. Tachibana, S.-C. Kuo, E. Hamel, T. Hackl, and K.-H. Lee J. Med. Chem. 41 1998 1155
4. O. Prakash, D. Kumar, R.K. Saini, and S.P. Singh Synth. Commun. 24 1994 2167
5. O.V. Singh, and R.S. Kapil Synth. Commun. 23 1993 277
6. V.N. Kalinin, M.V. Shostakovsky, and A.B. Ponomaryov Tetrahedron Lett. 33 1992 373
7. S. Torii, H. Okumoto, and X.L. He Tetrahedron Lett. 32 1991 237
8. O.E.O. Hormi, C. Peltonen, and L. Heikkila J. Org. Chem. 55 1990 2513
9. J.A. Donnelly, and D.F. Farrell Tetrahedron 46 1990 885
10. J.A. Donnelly, and D.F. Farrell J. Org. Chem. 55 1990 1757
11. A.L. Tokes, and G. Litkei Synth. Commun. 23 1993 895 and references cited therein
12. A.L. Tokes, and L. Szilagyi Synth. Commun. 17 1987 1235
13. A.L. Tokes, G. Litkei, and L. Szilagyi Synth. Commun. 22 1992 2433
14. K.H. Kumar, D. Muralidharan, and P.T. Perumal Synthesis 2004 63
15. R.S. Varma, and R.K. Saini Synlett 1997 857
16. W. Miao, and T.H. Chan Org. Lett. 26 2003 5
17. C.M. Gordon Appl. Catal. A 222 2001 101
18. H. Olivier-Bourbigou, and L. Magna J. Mol. Catal. A: Chem. 419 2002 182
19. Rogers, R. D.; Seddon, K. R. In Ionic Liquids as Green Solvents: Progress and Prospects; Rogers, R. D., Seddon, K. R., Eds.; ACS Symposium Series 856; American Chemical Society: Washington, DC, 2003.
20. P. Wasserscheid, and T. Welton Ionic Liquids in Synthesis 2003 Wiley-VCH Weinheim
21. M.T. Reetz, W. Wiesenhöefer, G. Francio, and W. Leitner Chem. Commun. 2002 992
22. T. Welton Chem. Rev. 99 1999 2071
23. M.J. Earle, and K.R. Seddon Pure Appl. Chem. 72 2000 1391
24. P. Wasserscheid, and W. Keim Angew. Chem., Int. Ed. 39 2000 3773
25. R. Sheldon Chem. Commun. 2001 2399
26. S. Chowdhury, R.S. Mohanb, and J.L. Scotta Tetrahedron 63 2007 2363
27. M. Picquet, S. Stutzmann, I. Tkatchenko, I. Tommasi, J. Zimmermann, and P. Wasserscheid Green Chem. 5 2003 153
28. J.S. Yadav, B.V.S. Reddy, G. Baishya, K.V. Reddy, and A.V. Narsaiah Tetrahedron 61 2005 9541
29. S.A. Forsyth, H.Q.N. Gunaratne, C. Hardacre, A. McKeown, D.W. Rooney, and K.R. Seddon J. Mol. Catal. A: Chem. 231 2005 61
30. For reviews, see: J. Dupont, R.F. De Souza, and P.A.Z. Suarez Chem. Rev. 102 2002 3667
31. P. Wasserscheid, and W. Keim Angew. Chem., Int. Ed. 39 2000 3772
32. S.H. Schoefer, N. Kaftzik, P. Wasserscheid, and U. Kragl Chem. Commun. 2001 425
33. P. Lozano, T. Diego, D. Carrié, M. Vaultier, and J.L. Iborra Chem. Commun. 2002 692
34. F. Van Rantwijk, R.M. Lau, and R. Sheldon Trends Biotechnol. 21 2003 131
35. M.J. Earle, S.P. Katdare, and K.R. Seddon Org. Lett. 6 2004 707
36. Rogers R. D.; Seddon, K. R. in Ionic Liquids: Industrial Applications to Green Chemistry; Rogers, R. D.; Seddon, K. R. Eds.; ACS Symposium Series 818; American Chemical Society: Washington, DC, 2002; pp xiii.
37. J.S. Yadav, B.V.S. Reddy, B. Eshwaraiah, M. Srinivas, and P. Vishnumirithy New J. Chem. 27 2003 462
38. M. Freemantle Chem. Eng. News 76 1998 32
39. Y. Chauvin, and H. Olivier B. Cornils, W.A. Herrmann, Applied Homogeneous Catalysis with Organometallic Compounds Vol. 1 1996 Wiley-VCH New York 245
40. Chauvin, Y.; De Souza, R. F.; Olivier, H. US Patent 5723,712, 1996; Chem. Abstr. 1999, 126, 173356u.
41. J. Fraga-Dubreuil, and J.P. Bazureau Tetrahedron Lett. 42 2001 6097 6100
42. J.R. Harjani, S.J. Nara, and M.M. Salunkhe Tetrahedron Lett. 43 2002 1127
43. V.V. Namboodiri, and R.S. Varma J. Chem. Soc., Chem. Commun. 2002 342
44. W. Sun, C.-G. Xia, and H.-W. Wang Tetrahedron Lett. 44 2003 2409
45. K. Qiao, and C. Yakoyama Chem. Lett. 33 2004 472
46. B.C. Ranu, A. Das, and S. Samanta J. Chem. Soc., Perkin Trans. 1 2002 1520
47. B.C. Ranu, and S.S. Dey Tetrahedron Lett. 44 2003 2865
48. B.C. Ranu, and S. Banerjee J. Org. Chem. 70 2005 4517
49. B.C. Ranu, S.S. Dey, and A. Hajra Tetrahedron 59 2003 2417
50. B.C. Ranu, and S.S. Dey Tetrahedron 60 2004 4183
51. J.S. Yadav, B.V.S. Reddy, and G. Baishya J. Org. Chem. 68 2003 7098
52. L.-W. Xu, J.-W. Li, S.-L. Zhou, and C.-G. Xia New J. Chem. 28 2004 188
53. M.L. Kantam, V. Neeraja, B. Kavita, B. Neelima, M.K. Chaudhuri, and S. Hussain Adv. Synth. Catal. 347 2005 763
54. H. Hayour, A. Bouraiou, S. Bouacida, F. Berrée, B. Carboni, T. Roisnel, and A. Belfaitah Tetrahedron Lett. 52 2011 4868
55. M. Chelghoum, M. Bahnous, S. Bouacida, T. Roisnel, and A. Belfaitah Acta Cryst. E67 2011 o1890
56. A. Bouraiou, F. Berrée, S. Bouacida, B. Carboni, A. Debache, T. Roisnel, and A. Belfaitah Lett. Org. Chem. 8 2011 374
57. A. Bouraiou, A. Debbache, S. Rhouati, B. Carboni, and A. Belfaitah J. Heterocycl. Chem. 45 2008 329
58. H. Menasra, A. Kedjadja, S. Rhouati, B. Carboni, and A. Belfaitah Synth. Commun. 35 2005 2779
59. 3, F(0 0 0) = 472, crystal size: 0.37 × 0.22 × 0.16 mm. Crystallographic data (excluding structure factors) for compound 2a have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 827683. This data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
60. N. Ahmed, and J.E. van Lier Tetrahedron Lett. 47 2006 2725
61. S. Chandrasekhar, K. Vijeender, and Ch. Sridhar Tetrahedron Lett. 48 2007 4935