Building Dihydropyrimidine Libraries via Microwave-Assisted Biginelli Multicomponent Reactions

Methods in Enzymology

Volumn 369, Issue , 2003, Pages 197-223

  Kappe, C Oliver ^a   Stadler, Alexander ^a  

^a UNIVERSITY OF GRAZ   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

DIHYDROPYRIMIDINE DERIVATIVE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIGINELLI MULTICOMPONENT REACTION; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; LIBRARY; MICROWAVE RADIATION; POLYMERIZATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 0346847647     PISSN: 00766879     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S0076-6879(03)69011-7     Document Type: Article

References (60)

1. I. Ugi, A. Dömling, and W. Hörl, Endeavour 18, 115 (1994).
2. R. W. Armstrong, A. P. Combs, P. A. Tempest, S. D. Brown, and T. A. Keating, Acc. Chem. Res. 29, 123 (1996).
3. L. F. Tietze and M. E. Lieb, Curr. Opin. Chem. Biol. 2, 363 (1998).
4. S. L. Dax, J. J. McNally, and M. A. Youngman, Curr. Med. Chem. 6, 255 (1999).
5. A. Dömling, Comb. Chem. High Throughput Screen. 1, 1 (1998).
6. M. Plunkett and J. A. Ellman, Sci. Am. 276, 68 (1997).
7. L. Weber, K. Illgen, and M. Almstetter, Synlett 366 (1999).
8. P. Biginelli, Gazz. Chim. Ital. 23, 360 (1893).
9. C. O. Kappe, Tetrahedron 49, 6937 (1993).
10. C. O. Kappe, Acc. Chem. Res. 33, 879 (2000).
11. C. O. Kappe, Eur. J. Med. Chem. 35, 1043 (2000).
12. K. S. Atwal, B. N. Swanson, S. E. Unger, D. M. Floyd, S. Moreland, A. Hedberg, and B. C. O'Reilly, J. Med. Chem. 34, 806 (1991).
13. G. C. Rovnyak, K. S. Atwal, A. Hedberg, S. D. Kimball, S. Moreland, J. Z. Gougoutas, B. C. O'Reilly, J. Schwartz, and M. F. Malley, J. Med. Chem. 35, 3254 (1992).
14. G. J. Grover, S. Dzwonczyk, D. M. McMullen, D. E. Normandin, C. S. Parham, P. G. Sleph, and S. Moreland, J. Cardiovasc. Pharm. 26, 289 (1995).
15. J. C. Barrow, P. G. Nantermet, H. G. Selnick, K. L. Glass, K. E. Rittle, K. F. Gilbert, T. G. Steele, C. F. Homnick, R. M. Freidinger, R. W. Ransom, P. Kling, D. Reiss, T. P. Broten, T. W. Schorn, R. S. L. Chang, S. S. O'Malley, T. V. Olah, J. D. Ellis, A. Barrish, K. Kassahun, P. Leppert, D. Nagarathnam, and C. Forray, J. Med. Chem. 43, 2703 (2000).
16. T. U. Mayer, T. M. Kapoor, S. J. Haggarty, R. W. King, S. L. Schreiber, and T. J. Mitchison, Science 286, 971 (1999).
17. L. Heys, C. G. Moore, and P. J. Murphy, Chem. Soc. Rev. 29, 57 (2000).
18. A. D. Patil, N. V. Kumar, W. Kokke, M. F. Bean, A. J. Freyer, C. De Brosse, S. Mai, A. Truneh, D. J. Faulkner, B. Carte, A. L. Breen, R. P. Hertzberg, R. K. Johnson, J. W. Westley, and B. C. M. Potts, J. Org. Chem. 60, 1182 (1995).
19. K. Lewandowski, P. Murer, F. Svec, and J. M. J. Fréchet, Chem. Commun. 2237 (1998).
20. K. Lewandowski, P. Murer, F. Svec, and J. M. J. Fréchet, J. Comb. Chem. 1, 105 (1999).
21. A. Dondoni and A. Massi, Tetrahedron Lett. 42, 7975 (2001).
22. P. Wipf and A. Cunningham, Tetrahedron Lett. 36, 7819 (1995).
23. A. Studer, S. Hadida, R. Ferritto, S.-Y. Kim, P. Jeger, P. Wipf, and D. P. Curran, Science 275, 823 (1997).
24. A. Studer, P. Jeger, P. Wipf, and D. P. Curran, J. Org. Chem. 62, 2917 (1997).
25. M. G. Valverde, D. Dallinger, and C. O. Kappe, Synlett 741 (2001).
26. L. D. Robinett, K. M. Yager, and J. C. Phelan, 211th National Meeting of the American Chemical Society, New Orleans, 1996, ORGN 122. American Chemical Society, Washington, DC, 1996.
27. C. O. Kappe, Bioorg. Med. Chem. Lett. 10, 49 (2000).
28. P. Lidström, J. Tierney, B. Wathey, and J. Westman, Tetrahedron 57, 9225 (2001).
29. C. Gabriel, S. Gabriel, E. H. Grant, B. S. J. Halstead, and D. M. P. Mingos, Chem. Soc. Rev. 27, 213 (1998).
30. A. de la Hoz, A. Diaz-Ortis, A. Moreno, and F. Langa, Eur. J. Org. Chem. 3659 (2000).
31. R. S. Varma, J. Heterocycl. Chem. 36, 1565 (1999).
32. N. Elander, J. R. Jones, S.-Y. Lu, and S. Stone-Elander, Chem. Soc. Rev. 29, 239 (2000).
33. M. Larhed, C. Moberg, and A. Hallberg, Acc. Chem. Res. 35, 717 (2002).
34. A. Loupy, A. Petit, J. Hamelin, F. Texier-Boullet, P. Jacquault, and D. Mathé, Synthesis 1213 (1998).
35. S. Deshayes, M. Liagre, A. Loupy, J.-L. Luche, and A. Petit, Tetrahedron 55, 10851 (1999).
36. M. Larhed and A. Hallberg, Drug Discov. Today 6, 406 (2001).
37. J. L. Krstenansky and I. Cotterill, Curr. Opin. Drug Discov. Dev. 4, 454 (2000).
38. A. Lew, P. O. Krutzik, M. E. Hart, and A. R. Chamberlin, J. Comb. Chem. 4, 95 (2002).
39. C. O. Kappe, Curr. Opin. Chem. Biol. 6, 314 (2002).
40. L. Perreux and A. Loupy, Tetrahedron 57, 9199 (2001).
41. A. Loupy, "Microwaves in Organic Synthesis." Wiley-VCH, Weinheim, 2002.
42. R. Gupta, A. K. Gupta, S. Paul, and P. L. Kachroo, Ind. J. Chem. 34B, 151 (1995).
43. A. Dandia, M. Saha, and H. Taneja, J. Fluorine Chem. 90, 17 (1998).
44. J. S. Yaday, B. V. Subba Reddy, E. Jagan Reddy, and T. Ramalingam, J. Chem. Res. 354 (2000).
45. S. J. Tu, J. F. Zhou, P. J. Cai, H. Wang, and J. C. Feng, Synth. Commun. 32, 147 (2002).
46. A. Stadler and C. O. Kappe, J. Chem. Soc. Perkin Trans. 1, 1363 (2000).
47. R. Gupta, S. Paul, and A. K. Gupta, Ind. J. Chem. Technol. 5, 340 (1998).
48. J. L. Krstenansky and Y. Khmelnitsky, Bioorg. Med. Chem. 7, 2157 (1999).
49. H. A. Stefani and P. M. Gatti, Synth. Commun. 30, 2165 (2000).
50. C. O. Kappe, D. Kumar, and R. S. Varma, Synthesis 1799 (1999).
51. M. Nüchter, W. Lautenschläger, B. Ondruschka, and A. Tied, LaborPraxis 25, 28 (2001).
52. A. Stadler and C. O. Kappe, J. Comb. Chem. 3, 624 (2001).
53. C. O. Kappe and A. Stadler, Org. React. 63, (2003).
54. C. O. Kappe, J. Org. Chem. 62, 7201 (1997).
55. Y. Ma, C. Qian, L. Wang, and M. Yang, J. Org. Chem. 65, 3864 (2000).
56. B. C. Ranu, A. Hajra, and U. Jana, J. Org. Chem. 65, 6270 (2000).
57. J. Lu, Y. Bai, Z. Wang, B. Yang, and H. Ma, Tetrahedron Lett. 41, 9075 (2000).
58. J. Lu and H. Ma, Synlett 63 (2000).
59. A. Stadler, S. Pichler, G. Horeis, and C. O. Kappe, Tetrahedron 58, 3177 (2002).
60. PersonalChemistry AB, Kungsgatan 76, SE-753 18 Uppsala, Sweden; phone: (internat.) +46-18-4899000; fax: (internat.) 46-18-4899100; http://www.personalchemistry.com.