Microwave-assisted solid-supported alkyne cyclotrimerization reactions for combinatorial chemistry douglas

Journal of Combinatorial Chemistry

Volumn 9, Issue 5, 2007, Pages 735-738

  Young, D ^a   Sripada, Lakshminath ^a   Deiters, Alexander ^a  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE;

CHEMISTRY; COMBINATORIAL CHEMISTRY; CYCLIZATION; MICROWAVE RADIATION; REVIEW;

ALKYNES; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; MICROWAVES;

EID: 34948908719     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc070068b     Document Type: Review

References (37)

1. (a) Chopade, P. R.; Louie, J. Adv. Synth. Cat. 2006, 348, 2307.
2. (b) Kotha, S.; Brahmachary, E.; Lahiri, K. Eur. J. Org. Chem. 2005, 4741.
3. (c) Yamamoto, Y. Curr. Org. Chem. 2005, 9, 503.
4. (d) Varela, J. A.; Saa, C. Chem. Rev. 2003, 103, 3787.
5. (e) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901.
6. (f) Schore, N. E. [2+2+2] Cycloadditions. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, p 1129.
7. (g) Vollhardt, K. P. C. Angew. Chem., Int. Ed. 1984, 23, 539.
8. (a) Tanaka, K.; Suzuki, N.; Nishida, G. Eur. J. Org. Chem. 2006, 3917.
9. (b) McCormick, M. M.; Duong, H. A.; Zuo, G.; Louie, J. J. Am. Chem. Soc. 2005, 127, 5030.
10. (c) Gutnov, A.; Heller, B.; Fischer, C.; Drexler, H. J.; Spannenberg, A.; Sundermann, B.; Sundermann, C. Angew. Chem., Int. Ed. 2004, 43, 3795.
11. Yamamoto, Y.; Arakawa, T.; Ogawa, R.; Itoh, K. J. Am. Chem. Soc. 2003, 125, 12143.
12. (a) Anderson, E. A.; Alexanian, E. J.; Sorensen, E. J. Angew. Chem., Int. Ed. 2004, 43, 1998.
13. (b) Witulski, B.; Zimmermann, A.; Gowans, N. D. Chem. Commun. 2002, 2984.
14. (c) Eichberg, M. J.; Dorta, R. L.; Grotjahn, D. B.; Lamottke, K.; Schmidt, M.; Vollhardt, K. P. J. Am. Chem. Soc. 2001, 123, 9324.
15. (d) Earl, R. A.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1983, 105, 6991.
16. (e) Sternberg, E. D.; Vollhardt, K. P. C. J. Org. Chem. 1982, 47, 3447.
17. Brandli, C.; Ward, T. R. J. Comb. Chem. 2000, 2, 42.
18. Grigg, R.; Scott, R.; Stevenson, P. J. Chem. Soc, Perkins Trans. 1 1988, 1357.
19. Senaiar, R. S.; Young, D. D.; Deiters, A. Chem. Commun. 2006, 1313.
20. Young, D. D.; Senaiar, R. S.; Deiters, A. Chem.-Eur. J. 2006, 12, 5563.
21. (a) Kappe, C. O.; Dallinger, D. Nat. Rev. Drug. Discover. 2006, 5, 51.
22. (b) Kappe, C. O. Angew. Chem., Int. Ed. 2004, 43, 6250.
23. (c) Loupy, A., Ed. Microwaves in Organic Synthesis, 2nd ed.; Wiley-VCH: Weinheim, 2006. For recent examples of microwave-mediated, solution-phase, cobaltcatalyzed cyclotrimerizations leading to pyridines, see:
24. (d) Zhou, Y.; Porco, J. A.; Snyder, J. K. Org. Lett. 2007, 9, 393.
25. (e) Hrdina, R.; Kadlcikova, A.; Valterova, I.; Hodacova, J.; Kotora, M. Tetrahedron Asym. 2006, 17, 3185.
26. (a) Gleiter, R.; Rittinger, S.; Langer, H. Chem. Ber. 1991, 124, 357.
27. (b) Fox, H. H.; Wolf, M. O.; Odell, R.; Lin, B. L.; Schrock, R. R.; Wrighton, M. S. J. Am. Chem. Soc. 1994, 116, 2827.
28. (c) Miyata, O.; Nakajima, E.; Naito, T. Chem. Pharm. Bull. 2001, 49, 213.
29. Ren, X. F.; Turos, E.; Lake, C. H.; Churchill, M. R. J. Org. Chem. 1995, 60, 6468.
30. (a) Delgado, M.; Janda, K. D. Curr. Org. Chem. 2002, 6, 1031.
31. (b) Guillier, F.; Orain, D.; Bradley, M. Chem. Rev. 2000, 100, 2091.
32. (c) James, I. W. Tetrahedron 1999, 55, 4855.
33. Sun, Q.; Zhou, X. M.; Islam, K.; Kyle, D. J. Tetrahedron Lett. 2001, 42, 6495.
34. (a) Larsen, S. D.; Hester, M. R.; Craig Ruble, J.; Kamilar, G. M.; Romero, D. L.; Wakefield, B.; Melchior, E. P.; Sweeney, M. T.; Marotti, K. R. Bioorg. Med. Chem. Lett. 2006, 16, 6173.
35. (b) He, Y.; Yang, J.; Wu, B.; Risen, L.; Swayze, E. E. Bioorg. Med. Chem. Lett. 2004, 14, 1217.
36. (c) Paget, S. D.; Foleno, B. D.; Boggs, C. M.; Goldschmidt, R. M.; Hlasta, D. J.; Weidner-Wells, M. A.; Werblood, H. M.; Wira, E.; Bush, K.; Macielag, M. J. Bioorg. Med. Chem. Utt. 2003, 13, 4173.
37. Fugmann, B.; Lang-Fugmann, S.; Steglich, W.; Adam, G. Römpp Encyclopedia of Natural Products; Thieme: Stuttgart and New York, 2000.