An alternative quinoline synthesis by via Friedländer reaction catalyzed by Yb(OTf)3

Tetrahedron Letters

Volumn 52, Issue 27, 2011, Pages 3474-3477

  Genovese, Salvatore ^a   Epifano, Francesco ^a   Marcotullio, Maria Carla ^b   Pelucchini, Caroline ^b   Curini, Massimo ^b  

^a UNIVERSITY OF CHIETI   (Italy)

^b UNIVERSITY OF PERUGIA   (Italy)

Author keywords

2 Aminobenzophenone; Acetylacetone; Quinolines; Yb(OTf)3

Indexed keywords

QUINOLINE DERIVATIVE; YTTERBIUM;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 79957973023     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.04.109     Document Type: Article

References (50)

1. O. Bilker, V. Lindo, M. Panico, A.E. Etiene, T. Paxton, a. Dell, M. Rogers, R.E. Sinden, and H.R. Morris Nature 392 1998 289 292
2. G. Roma, M.D. Braccio, G. Grossi, F. Mattioli, and M. Ghia Eur. J. Med. Chem. 35 2000 1021 1035
3. Y.L. Chen, K.C. Fank, J.Y. Sheu, S.L. Hsu, and C.C. Tzeng J. Med. Chem. 44 2001 2374 2377
4. J.P. Michael Nat. Prod. Rep. 18 2001 543 549
5. A.K. Aggarwal, and S.A. Jenekhe Macromolecules 24 1991 6806 6808
6. X. Zhang, A.S. Shetty, and S.A. Jenekhe Macromolecules 32 1999 7422 7429
7. S.A. Jenekhe, L. Lu, and M.M. Alam Macromolecules 34 2001 7315 7324
8. W. Du, and D.P. Curran Org. Lett. 5 2003 1765 1768
9. D.M. Lindsay, W. Dohle, A.E. Jensen, F. Kopp, and P. Knochel Org. Lett. 4 2002 1819 1822
10. M. Matsugi, F. Tabusa, and J. Minamikawa Tetrahedron Lett. 41 2000 8523 8525
11. P.G. Dormer, K.K. Eng, R.N. Farr, G.R. Humphrey, J.C. McWilliams, P.J. Reider, J.W. Sager, and R.P. Volante J. Org. Chem. 68 2003 467 477
12. P. Friedländer Ber. Dtsch. Chem. Ges. 15 1882 2572 2575
13. R.C. Elderfield R.C. Elderfield, Heterocyclic Compounds Vol. 4 1952 Wiley New York 45 57
14. J.I. Ubeda, M. Villacampa, and C. Avendano Synthesis 1998 1176 1180
15. J. Wu, H.G. Xia, and K. Gao Org. Biomol. Chem. 4 2006 126 129
16. L. Strekowski, and A. Czamy J. Fluoresc. Chem. 104 2000 281 284
17. Y.Z. Hu, G. Zang, and R.P. Thummel Org. Lett. 5 2003 2251 2253
18. A. Arcadi, M. Chiarini, S. Giuseppe, and F. Marinelli Synlett 2003 203 206
19. J.S. Yadav, B.V.S. Reddy, and K. Premalatha Synlett 2004 963 966
20. S.K. De, and R.A. Gibbs Tetrahedron Lett. 46 2005 1647 1649
21. P. Arumugam, G. Karthikeyan, R.D. Atchudan, and P.T.P. Muralidhran Chem. Lett. 34 2005 314 315
22. M.A. Zolfigol, P. Salehi, M. Shiri, T. Faal Rastegar, and A. Ghaderi J. Iran. Chem. Soc. 5 2008 490 497
23. D.S. Bose, and R.K. Kumar Tetrahedron Lett. 47 2006 813 816
24. S.V. Ryabukhin, D.M. Volochnyuk, A.S. Plaskon, V.S. Naumchik, and A.A. Tolomachev Synthesis 2007 1214 1224
25. S. Ghassamipour, and A.R. Sardarian Tetrahedron Lett. 50 2009 514 519
26. M. Dabiri, P. Salehi, M. Baghbanzadeh, and M. Shakouri-Nikcheh Tetrahedron Lett. 49 2008 5366 5368
27. For a recent review on the Friedländer annulation see J. Marco-Contelles, E. Pérez-Mayoral, A. Samadi, M. do Carmo Carreiras, and E. Soriano Chem. Rev. 109 2009 2652 2671
28. M. Curini, F. Epifano, M.C. Marcotullio, and O. Rosati Tetrahedron Lett. 42 2001 3193 3195
29. M. Curini, F. Epifano, M.C. Marcotullio, and O. Rosati Heterocycles 55 2001 1599 1604
30. M. Curini, F. Epifano, M.C. Marcotullio, and O. Rosati Eur. J. Org. Chem. 2002 1562 1565
31. M. Curini, F. Epifano, F. Maltese, and O. Rosati Tetrahedron Lett. 43 2002 4895 4897
32. M. Curini, F. Epifano, F. Maltese, and O. Rosati Synlett 2003 552 554
33. M. Curini, F. Epifano, F. Maltese, and M.C. Marcotullio Eur. J. Org. Chem. 2003 1631 1634
34. M. Curini, F. Epifano, F. Montanari, O. Rosati, and S. Taccone Synlett 2004 1832 1834
35. M. Curini, F. Epifano, S. Genovese, M.C. Marcotullio, and O. Rosati Org. Lett. 2005 1331 1333
36. M. Curini, F. Epifano, and S. Genovese Tetrahedron Lett. 47 2006 4697 4700
37. M. Curini, F. Epifano, and S. Genovese Tetrahedron Lett. 48 2007 2717 2720
38. S. Genovese, F. Epifano, C. Pelucchini, and M. Curini Eur. J. Org. Chem. 2009 1132 1135
39. S. Genovese, F. Epifano, C. Pelucchini, A. Procopio, and M. Curini Tetrahedron Lett. 51 2010 5992 5995
40. F. Epifano, S. Genovese, O. Rosati, S. Tagliapietra, C. Pelucchini, and M. Curini Tetrahedron Lett. 52 2011 568 571
41. J.M. Muchowski, and M.L. Maddox Can. J. Chem. 82 2004 461 478
42. 10NO: C, 77.62; H, 5.92; N, 16.46. Found: C, 77.67; H, 5.34; N, 16.99. The degree of purity of each product listed in the paper was analyzed by GC/MS with a Hewlett Packard 6890 gas chromatograph equipped with a 12.5 mm × 0.25 mm MetSil column couplet to HP Chem Station Software.
43. K.S. Pitzer Acc. Chem. Res. 12 1974 271 276
44. R. León, C. de los Ríos, J. Marco-Contelles, O. Huertas, X. Barril, F.J. Luque, M.G. López, and M. Villarroya Bioorg. Med. Chem. 16 2008 7759 7769 and references herein cited
45. R. Enugala, S. Nuvvula, V. Kotra, R. Varala, and S.R. Adapa Heterocycles 75 2008 2523 2533
46. R. Varala, R. Enugala, and S.R. Adapa Synthesis 2006 3825 3830
47. J.E. Na, K.Y. Lee, D.Y. Park, and J.N. Kim Bull. Korean Chem. Soc. 26 2005 323 355
48. N.P. Selvam, C. Saravanan, D. Muralidharan, and P.T. Perumal J. Heterocycl. Chem. 43 2006 1379 1382
49. H.M. Wang, R.S. Hou, H.T. Cheng, and L.C. Chen Heterocycles 78 2009 487 493
50. M.A. Ali Zolfigol, P. Salehi, A. Ghaderi, M. Shiri, and Z. Tanbakouchian J. Mol. Catal. A: Chem. 259 2006 253 258