Solid-phase synthesis of cleavable N-arylmaleimides: Applications in 1,3-dipolar cycloaddition and in thiol scavenging

Organic Letters

Volumn 3, Issue 22, 2001, Pages 3491-3494

  Hoveyda, Hamid R ^a,b   Hall, Dennis G ^b  

^a Néokimia Inc   (Canada)

^b UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000259831     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016533+     Document Type: Article

References (38)

1. See, for example: (a) Janda, K. D.; Ashtey, J. A.; Jones, T. M.; McLeod, D. A.; Schloeder, D. M.; Weinhouse, M. I. J. Am. Chem. Soc. 1990, 112, 8886.
2. (b) Smyth, G. E.; Colman, R. F. J. Biol. Chem. 1991, 266, 14918.
3. (c) Rusiecki, V. K.; Warne, S. A. Bioorg. Med. Chem. Lett. 1993, 3, 707.
4. (d) Hermanson, G. T. Bioconjugate Techniques; Academic Press: New York, 1996; p 148.
5. (e) Seelig, B.; Keiper, S.; Stuhlmann, F.; Jäschke, A. Angew. Chem., Int. Ed. 2000, 39, 4576.
6. Most recently, a method to anchor maleimide to trityl resin was reported: Barrett, A. G. M.; Boffey, R. J.; Frederiksen, M. U.; Newton, C. G.; Roberts, R. S. Tetrahedron Lett. 2001, 42, 5579.
7. Stevens, M. P.; Jenkins, A. D. J. Polym. Sci. 1979, 17, 3675.
8. Wang, X.; Parlow, J. J.; Porco, J. A. Org. Lett. 2000, 2, 3509.
9. For another preparation from aminomethyl polystyrene and maleic anhydride using dehydrative cyclization, see: Rebek, J., Jr.; Gaviña, F. J. Am. Chem. Soc. 1975, 97, 3453.
10. Tailor, J.; Hall, D. G. Org. Lett. 2000, 2, 3715.
11. For a comprehensive overview, see: Maleic Anhydride; Trivedi, B. C.; Culberton, B. M.; Plenum Press: New York, 1982.
12. For examples of solution-phase synthesis of maleimides, see: (a) Tawney, P. O.; Snyder, R. H.; Conger, R. P.; Leibbrand, K. A.; Stiteler, C. H.; Williams, A. R. J. Org. Chem. 1961, 26, 15 and references therein,
13. (b) Hargreaves, M. K.; Pritchard, J. G.; Dave, H. R. Chem. Rev. 1970, 70, 439 and references therein,
14. (c) Garner, P.; Ho, W. B.; Grandhee, S. K.; Youngs, W. J.; Kennedy, W. O. J. Org. Chem. 1991, 56, 5893 and references therein.
15. (d) Braish, T. F.; Fox, D. E. Synlett 1992, 979.
16. (e) Clevenger, R. C.; Turnbull, K. D. Synth. Commun. 2000, 30, 1379.
17. (a) Walker, M. A. Tetrahedron Lett. 1994, 35, 665.
18. (b) Walker, M. A. J. Org. Chem. 1995, 60, 5352.
19. (a) Landini, D.; Rolla, F. Synthesis 1976, 389.
20. (b) Sato, T.; Otera, J. Synlett 1995, 336.
21. (a) Stenzenberger, H. In Polyimides; Wilson, D., Stenzenberger, H. D., Hergenrother, P. M., Eds.; Blackie: Glasgow, 1990; p 79.
22. (b) Liu, F. J.; Munukutta, S.; Levon, K.; Tesoro, G. J. Polym. Sci., Part A: Polym. Chem. 1992, 30, 157 and references therein.
23. In stark contrast, use of DIC/DMAP procedures for the cyclization step was unsuccessful, giving a complex mixture of products.
24. The resin loading was estimated by combustion analysis of the nitrogen content on the resin, and the results indicated a loading in excess of 90% in the cases of all three linkers reported herein. Estimated values of resin loading and homogeneity of cleaved maleimides were also assessed from nonoptimized weight yields after acidic cleavage (characterized by NMR, and LCMS): p-MBA, 100%; m-MBA, 90%; Br-MBA, 70%).
25. (a) Hamper, B. C.; Dukesherer, D. R.; South, M. S. Tetrahedron Lett. 1996, 37, 3671.
26. (b) Bicknell, A. J.; Hird, N. W. Biorg. Med. Chem. Lett. 1996, 6, 2441.
27. For general reviews on 1,3-dipolar cycloaddition, see: (a) Grigg, R. Chem. Soc. Rev. 1987, 16, 89.
28. (b) Tsuge, O.; Kanemasa, S. Adv. Heterocycl. Chem. 1989, 45, 231.
29. (c) Padwa, A. Intermolecular 1,3-Dipolar Cycloadditions. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. IV, p 1069.
30. For other recent applications of 1,3-dipolar cycloaddition on solid support, see: (a) Costero, A. M.; Pitarch, M.; Luz Cano, M. J. Chem. Res., Synop. 1994, 316.
31. (b) Murphy, M.; Schullek, J. R.; Gordon, E. M.; Gallop, M. A. J. Am. Chem. Soc. 1995, 117. 7029.
32. (c) Kantorowski, E. J.; Kurth, M. J. Mol. Diversity 1996, 2, 207.
33. (d) Hollinshead, S. P. Tetrahedron Lett. 1996, 37, 9157.
34. (e) Peng, G.; Sohn, A.; Gallop, M. A. J. Org. Chem. 1999, 64, 8342.
35. Tsuge, O.; Kanemasa, S.; Yoshioka, M. J. Orig. Chem. 1988, 53, 1384.
36. (a) Booth, R. J.; Hodges, J. C. Acc. Chem. Res. 1999, 32, 18.
37. (b) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 23, 3815.
38. (c) Eames, J.; Watkinson, M. Eur. J. Org. Chem. 2001, 1213.