Synthesis of 1-alkyl-4-imidazolecarboxylates: A catch and release strategy

Journal of Combinatorial Chemistry

Volumn 7, Issue 6, 2005, Pages 905-908

  De Luca, Lidia ^a   Giacomelli, Giampaolo ^a   Porcheddu, Andrea ^a  

^a UNIVERSITY OF SASSARI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 28244445161     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc050067o     Document Type: Article

References (36)

1. (a) Heeres, J.; Backx, L. J. J.; Mostmanns, J. H.; van Cutsem, J. J. Med. Chem. 1979, 22, 1003-1005.
2. (b) Saha, A. K.; Liu, L.; Simoneaux, R. L.; Kukla, M. J.; Marichal, P.; Odds, F. Bioorg. Med. Chem. Lett. 2000, 10, 2175-2178.
3. Hunkeler, W.; Möhler, H.; Pieri, L.; Polc, P.; Bonetti, E. P.; Cumin, R.; Schaffner, R.; Haefely, W. Nature 1981, 290, 514-516.
4. (a) Heerding, D: A.; Chan, G.; DeWolf, W. E., Jr.; Fosberry, A. P.; Janson, C. A.; Jaworki, D. D.; McManus, E.; Miller, W. H.; Moore, T. D.; Payne, D. J.; Qiu, X.; Rittenhouse, S. F.; Slater-Radosti, C.; Smith, W.; Takata, D. T.; Vaidya, K. S.; Yuan, C. C. K.; Huffman, W. F. Bioorg. Med. Chem. Lett. 2001, 11, 2061-2065.
5. (b) Khabnadideh, S:; Rezaei, Z.; Khalafi-Nezhad, A.; Bahrinajafi, R.; Mohamadi, R.; Farrokhroz, A. A. Bioorg. Med. Chem. Lett. 2003, 13, 2863-2865.
6. Brogden, R. N.; Heel, R. C.; Speigt. T. M. Drugs 1978, 16, 387-417.
7. For example, see: (a) Ebel, K. in Houben-Weyl: Methoden der organischen Chemie, Hetarene III, 1H-Imidazole; Schaumann, E.; Ed.; Georg-Thieme: Stuttgart, NY, 1994, pp 1-215.
8. (b) Bilodeau, M. T.; Cunnigham, A. M. J. Org. Chem. 1998, 63, 2800-2801.
9. (c) Njar, V. C. O. Synthesis 2000, 2019-2028.
10. (d) Alanine, A.; Capretta, A. Tetrahedron Lett. 2002, 43, 7687-7690.
11. Helal, C. J.; Lucas, J. C. Org. Lett. 2002, 4, 4133-4134.
12. Bienaymé, H.; Bouzid, K. Tetrahedron Lett. 1998, 39, 2735-2738.
13. Henkel, B.; Sax, M.; Dömling, A. Tetrahedron Lett. 2003, 44, 3679-3682 and references therein.
14. Henkel, B.; Westner, B.; Dömling, A. Synlett 2003, 2410-2412.
15. Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168-3186.
16. Henkel, B. Tetrahedron Lett. 2004, 45, 2219-2221.
17. For an excellent book and reviews, see: (a) Nicolau, K. C. Handbook of Combinatorial Chemistry; Wiley-VCH: Weinheim, 2002.
18. (b) Zaragozza Dorwald, F. Solid-Phase Synthesis; Wiley-VCH: Weinheim, 2000.
19. (c) Jung, G. Combinatorial Chemistry; Wiley-VCH: Weinheim, 1999.
20. (d) DeWitt, S. H.; Czarnik, A. W. A Pratical Guide to Combinatorial Chemistry; American Chemistry Society: Washington, 1997.
21. Strohmeier, G. A.; Reidlinger, C.; Kappe, C. O. QSAR Comb. Sci. 2005, 3, 364-377.
22. (b) Siu, J.; Baxendale, I. R.; Lewthwaite, R. A.; Ley, S. V. Org., Biomol. Chem. 2005, 3, 3140-3160.
23. (c) Ciolli, C. J.; Kalagher, S.; Belshaw, P. J. Org. Lett. 2004, 6, 1891-1894.
24. (d) Vickerstaffe, E.; Warrington, B. H.; Ladlow, M.; Ley, S. V. J. Comb. Chem. 2002, 6, 332-339.
25. (e) Newcombe, N.; Bradley, M. Tetrahedron, 2003, 59, 10213-10222.
26. (f) Lin, Y. S.; Hsu, N. M. J. Comb. Chem. 2002, 3, 634-643.
27. (g) Beech, C. L.; Coope, J. F.; Fairley, G.; Gilbert, P. S.; Main, B. G.; Ple, K. J. Org. Chem. 2001, 66, 2240-2245.
28. (h) Orain, D.; Bradley, M. Mol. Diversity 2000, 5, 25-34.
29. (a) De Luca, L.; Giacomelli, G.; Porcheddu, A.; Salaris, M.; Taddei, M. J. Comb. Chem. 2003, 5, 465-471.
30. (b) Porcheddu, A.; Giacomelli, G.; De Luca, L.; Ruda, A. M. J. Comb. Chem. 2004, 6, 105-111.
31. (c) Porcheddu, A.; Giacomelli, G.; Chighine, A.; Masala, S. Org. Lett. 2004, 6, 4925-4927.
32. For reviews on microwave-assisted combinatorial chemistry, see, for example, the following: (a) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, A. R. J. Comb. Chem. 2002, 4, 95-105.
33. (b) Kappe, C. O. Curr. Opin. Chem. Biol. 2002, 6, 314-320.
34. The MW experiments were performed in a self-tuning single mode CEM Discover Focused Synthesizer apparatus. The instrument continuously adjusted the applied wattage to maintain the desired temperature.
35. Vojkovsky, T. Pept. Res. 1995, 8, 236-237
36. Battersby, A. R.; Nicoletti, M.; Staunton, J.; Vleggaar, R. J. Chem. Soc., Perkin Trans. 1 1980, 43-51.