Applications of multicomponent assembly processes to the facile syntheses of diversely functionalized nitrogen heterocycles

Heterocycles

Volumn 84, Issue 2, 2012, Pages 1089-1112

  Donald, James R ^a   Granger, Brett A ^a   Hardy, Simon ^a   Sahn, James J ^a   Martin, Stephen F ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84856557094     PISSN: 03855414     EISSN: 18810942     Source Type: Journal    
DOI: 10.3987/COM-11-S(P)92     Document Type: Article

References (64)

1. For the origin of the term "privileged scaffolds", see: B. E. Evans, K. E. Rittle, M. G. Bock, R. M. DiPardo, R. M. Freidinger, W. L. Whitter, G. F. Lundell, D. F. Veber, P. S. Anderson, R. S. L. Chang, V. J. Lotti, D. J. Cerino, T. B. Chen, P. J. Kling, K. A. Kunkel, J. P. Springer, and J. Hirshfield, J. Med. Chem., 1988, 31, 2235.
2. For reviews on privileged scaffolds, see: (a) D. A. Horton, G. T. Bourne, and M. L. Smythe, Chem. Rev., 2003, 103, 893
3. R. W. DeSimone, K. S. Currie, S. A. Mitchell, J. W. Darrow, and D. A. Pippin, Comb. Chem. High Throughput Screening, 2004, 7, 473
4. L. Constantino and D. Barlocco, Curr. Med. Chem., 2006, 13, 65
5. M. E. Welsch, S. A. Snyder, and B. R. Stockwell, Curr. Opin. Chem. Biol., 2010, 14, 347.
6. S. F. Martin, B. Benage, and J. E. Hunter, J. Am. Chem. Soc., 1988, 110, 5925.
7. S. F. Martin, Acc. Chem. Res., 2002, 35, 895.
8. B. Cheng, J. D. Sunderhaus, and S. F. Martin, Org. Lett., 2010, 12, 3622.
9. J. D. Sunderhaus, C. Dockendorff, and S. F. Martin, Org. Lett., 2007, 9, 4223
10. J. D. Sunderhaus, C. Dockendorff, and S. F. Martin, Tetrahedron, 2009, 65, 6454
11. J. D. Sunderhaus and S. F. Martin, Chem. Eur. J., 2009, 15, 1300.
12. For preliminary accounts of some of this work, see: (a) J. R. Donald and S. F. Martin, Org. Lett., 2011, 13, 852
13. J. J. Sahn, J. Y. Su, and S. F. Martin, Org. Lett., 2011, 13, 2590
14. S. Hardy and S. F. Martin, Org. Lett., 2011, 13, 3102
15. B. A. Granger, K. Kaneda, and S. F. Martin, Org. Lett., 2011, 13, 4542.
16. I. Gavras, D. Vlahakos, J. C. Melby, and H. Gavras, J. Clin. Pharm., 1984, 24, 343.
17. T. Asaoka, K. Yazawa, Y. Mikami, and K. Takahashi, J. Antibiot., 1982, 35, 1708.
18. G. Francois, G. Bringmann, J. D. Phillipson, M. R. Boyd, L. A. Assi, C. Schneider, and G. Timperman, PCT Int. Appl. WO 9521616 A1 19951717.
19. D. E. Worrall, Org. Syn., 1929, 9, 66
20. R. W. Schumacher and B. S. Davidson, Tetrahedron, 1999, 55, 935
21. A. M. M. Mjalli, D. R. Gohimmukkulah, and S. Tyagi, PCT Int. Appl. WO 2006093823.
22. N. Slougui and G. Rousseau, Synth. Commun., 1987, 17, 1.
23. T. Kawate, M. Nakagawa, H. Yamazaki, M. Hirayama, and T. Hino, Chem. Pharm. Bull., 1993, 41, 287.
24. P. Cledera, C. Avendaño, and J. C. Menéndez, Tetrahedron, 1998, 54, 12349.
25. Y. Dong, J. Chollet, M. Vargas, N. R. Mansour, Q. Bickle, Y. Alnouti, J. Huang, J. Keiser, and J. L. Vennerstrom, Bioorg. Med. Chem. Lett., 2010, 20, 2481.
26. This procedure can be telescoped in a one pot procedure, although in preliminary experiments we found the yields were less reproducible.
27. For recent reviews on the use of !-amino nitriles in the generation of molecular diversity, see: (a) T. Opatz, Synthesis, 2009, 12, 1941
28. J. A. González-Vera, M. T. García-López, and R. Herranz, Mini-Rev. Org. Chem., 2008, 5, 209
29. D. Enders and J. P. Shilvock, Chem. Soc. Rev., 2000, 29, 359.
30. For a recent review, see: P. Galatsis, In Name Reactions for Functional Group Transformations, ed. by J. J. Li and E. J. Corey, Wiley: Hoboken, 2007, 477.
31. E. T. Pelkey and G. W. Gribble, Tetrahedron Lett., 1997, 38, 5603.
32. L. Bertelli, G. Biagi, I. Giorgi, O. Livi, C. Manera, V. Scartoni, C. Martini, G. Giannaccini, L. Trincavelli, and P. L. Barili, Farmaco, 1998, 53, 305.
33. C. del Pozo, A. Macías, F. López-Oritz, M. A. Maestro, E. Alonso, and J. González, Eur. J. Org. Chem., 2004, 535
34. P. D. Mehta, N. P. S. Sengar, and A. K. Pathak, Eur. J. Med. Chem., 2010, 45, 5541.
35. A. Salcedo, L. Neuville, and J. Zhu, J. Org. Chem., 2008, 73, 3600.
36. J. J. Baldwin, D. A. Claremon, J. M. Elliott, N. Liverton, D. C. Remy, and H. G. Selnick, Merck & Co. Inc., World Patent WO 9514471 (A1), 1995
37. J. J. Lynch Jr. Salata J.J. Merck & Co. Inc. World Patent WO 9800405 (A1), 1998.
38. J. V. Cooney and W. E. McEwen, J. Org. Chem., 1981, 46, 2570
39. J. V. Cooney, B. D. Beaver, and W. E. McEwen, J. Heterocycl. Chem., 1985, 22, 635.
40. G. V. De Lucca and M. J. Otto, Bioorg. Med. Chem. Lett., 1992, 2, 1639.
41. G. Broggini, L. Garanti, G. Molenti, and G. Zecchi, Heterocycles, 1999, 51, 1295.
42. M. Boulouard, A. C. Gillard, P. O. Guillaumat, M. Daoust, E. Legrand, M. A. Quermonne, and S. Rault, Pharm. Pharmacol. Commun., 1998, 4, 43.
43. D. Xiao, A. Palani, C. Wang, H.-C. Tsui, N.-Y. Shih, and G. A. Reichard, European Patent EP 1,747,221, 2005.
44. For the original report of this method to cleave 4-pentenamides, see: R. Madsen, C. Roberts, and B. Fraser-Reid, J. Org. Chem., 1995, 60, 7920.
45. For the only other known example of a tandem enolate arylation/alkylation process, see: R. R. Goehring, Y. P. Sachdeva, J. S. Pisipati, M. C. Sleevi, and J. F. Wolfe, J. Am. Chem. Soc., 1985, 107, 435.
46. R. Ferraccioli and D. Carenzi, Synthesis, 2003, 9, 1383.
47. For a similar reaction, using aryl iodides in conjunction with pre-formed thioureas, see: D. Orain, A.-C. Blumstein, E. Tasdelen, and S. Haessig, Synlett, 2008, 16, 2433.
48. S. Jones, J. Johnson, J. Ives, K. Hedberg, A. Dunaiskis, D. Chapin, J. Nielsen, D. Liston, and Y. L. Chen, J. Med. Chem., 1994, 37, 1996.
49. A. E. Jacobson and M. Mokotoff, J. Med. Chem., 1970, 13, 7.
50. L. S. Povarov, Russ. Chem. Rev., 1967, 36, 656
51. V. V. Kouznetsov, Tetrahedron, 2009, 65, 2721.
52. C. Xia, L. Heng, and D. Ma, Tetrahedron Lett., 2002, 43, 9405.
53. K. Minagawa, S. Kouzuki, and T. Kamigauchi, J. Antibiot., 2002, 55, 165.
54. D. K. Luci, E. C. Lawson, E. Ghosh, W. A. Kinny, C. E. Smith, J. Qi, Y. Wang, L. K. Minor, and B. E. Maryanoff, Tetrahedron Lett., 2009, 50, 4958.
55. M. L. Curtin, R. R. Frey, R. H. Heyman, K. A. Sarris, D. H. Steinman, J. H. Holmes, P. J. Bousquet, G. A. Cunha, M. D. Moskey, A. A. Ahmed, L. J. Pease, K. B. Glaser, K. D. Stewart, S. K. Davidsen, and M. R. Michaelides, Bioorg. Med. Chem. Lett., 2004, 14, 4505.
56. W. E. Parham and C. K. Bradsher, Acc. Chem. Res., 1982, 15, 300.
57. A. Hinschberger, S. Butt, B. Lelong, M. Boulouard, A. Dumuis, D. Francois, R. Bureau, B. Pfeiffer, P. Renard, and S. Rault, J. Med. Chem., 2003, 46, 138.
58. For example, see: F. F. Painter and K. T. Wanner, Tetrahedron, 1994, 50, 3113.
59. W. C. Still, M. Kahn, and A. Mitra, J. Org. Chem., 1978, 43, 2923.
60. C. A. Sperger and K. T. Wanner, Tetrahedron, 2009, 65, 5824.
61. A. O. King, E. Negishi, F. J. Villani, Jr., and A. Silveira, Jr., J. Org. Chem., 1978, 43, 358.
62. Y. Kawakamie, T. Aoki, and Y. Yamashita, Polym. Bull., 1987, 18, 473.
63. S. B. Rosenblum, T. Huynh, A. Afonso, and H. R. Davis Jr., Tetrahedron, 2000, 56, 5735.
64. E. Negishi, L. D. Boardman, S. Vahid, A. Bagheri, T. Stoll, J. M. Tour, and C. L. Rand, J. Am. Chem. Soc., 1988, 110, 5383.