Rapid synthesis of diketopiperazine macroarrays via Ugi four-component reactions on planar solid supports

Chemical Communications

Volumn , Issue 27, 2006, Pages 2884-2886

  Lin, Qi ^a   Blackwell, Helen E ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PIPERAZINEDIONE;

ARTICLE; CHEMICAL REACTION; SOLID; SYNTHESIS;

EID: 33746399361     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b604329a     Document Type: Article

References (19)

1. R. E. Dolle J. Comb. Chem. 2005 7 739 798
2. M. D. Burke E. M. Berger S. L. Schreiber Science 2003 302 613 618
3. S. V. Ley I. R. Baxendale Nat. Rev. Drug Discovery 2002 1 573 586
4. M. D. Bowman R. C. Jeske H. E. Blackwell Org. Lett. 2004 6 2019 2022
5. Q. Lin J. C. O'Neill H. E. Blackwell Org. Lett. 2005 7 4455 4458
6. M. D. Bowman M. M. Jacobson H. E. Blackwell Org. Lett. 2006 8 1645 1648
7. H. E. Blackwell Org. Biomol. Chem. 2003 1 1251 1255
8. C. O. Kappe D. Dallinger Nat. Rev. Drug Discovery 2006 5 51 63
9. G. D. Geske R. J. Wezeman A. P. Siegel H. E. Blackwell J. Am. Chem. Soc. 2005 127 12762 12763
10. M. T. G. Holden S. R. Chhabra R. de Nys P. Stead N. J. Bainton P. J. Hill M. Manefield N. Kumar M. Labatte D. England S. Rice M. Givskov G. P. C. Salmond G. S. A. B. Stewart B. W. Bycroft S. A. Kjelleberg P. Williams Mol. Microbiol. 1999 33 1254 1266
11. G. Degrassi C. Aguilar M. Bosco S. Zahariev S. Pongor V. Venturi Curr. Microbiol. 2002 45 250 254
12. M. C. Pirrung K. Das Sarma Tetrahedron 2005 61 11456 11472
13. A. K. Szardenings T. S. Burkoth H. H. Lu D. W. Tien D. A. Campbell Tetrahedron 1997 53 6573 6593
14. P. G. Wyatt M. J. Allen A. D. Borthwick D. E. Davies A. M. Exall R. J. D. Hatley W. R. Irving D. G. Livermore N. D. Miller F. Nerozzi S. L. Sollis A. K. Szardenings Bioorg. Med. Chem. Lett. 2005 15 2579 2582
15. C. Hulme M. M. Morrissette F. A. Volz C. J. Burns Tetrahedron Lett. 1998 39 1113 1116
16. T. A. Keating R. W. Armstrong J. Am. Chem. Soc. 1996 118 2574 2583
17. Acetylation was performed to both block any unreacted amines on the support and provide intermediates with improved stability for analysis
18. N. Zander Mol. Divers. 2004 8 189 195
19. 2 at 25°C. Compounds 10′ were the predominant products observed post-cleavage (ca. 70% conversion). We speculate that hydrolysis could occur faster than the cyclization reaction and/or be promoted by residual water in the cellulose support