Parallel synthesis of arrays of amino-acid-derived isocyanoamides useful as starting materials in IMCR

Journal of Combinatorial Chemistry

Volumn 8, Issue 6, 2006, Pages 872-880

  Dömling, Alexander ^a   Beck, Barbara ^b   Fuchs, Thilo ^b   Yazbak, Ahmad ^c  

^a ABC Pharma   (Germany)

^b Biovertis AG   (Germany)

^c Synthatex Ltd   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; AMINO ACID; CYANIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

AMIDES; AMINO ACIDS; CYANIDES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 33845266730     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc060068w     Document Type: Article

References (57)

1. (a) Dömling, A.; Ugi, I. Angew. Chem. Intl. Ed. 2000, 39, 3168.
2. (b) Dömling, A. Chem. Rev. 2006, 106, 17.
3. Lieke, W. Justus Liebigs Ann. Chem. 1859, 112, 316.
4. Hofmann, W. Justus Liebigs Ann. Chem. 1867, 144, 114.
5. Gautier, A. Ann. Chim. (Paris) 1869, 17, 218.
6. Meyer, E. J. Prakt. Chem. 1866, 147.
7. Skorna, G.; Ugi, I. Angew. Chem. Int. Ed. Engl. 1977, 16, 259.
8. O'Neil, A.; Baldwin, J. Synlett 1990, 603.
9. Gassman, P. G.; Guggenheim, T. L. J. Am. Chem. Soc. 1982, 104, 5849.
10. (a) Bossio, R.; Marcaccini, S.; Pepino, R.; Polo, C.; Torroba, T. J. Heterocycl. Chem. 1980, 17, 111.
11. (b) Chupp, J. P.; Leschinsky, K. L. Heterocycles 1989, 29, 1829.
12. (c) Zhou, X.-T.; Lin, Y.-R.; Dai, L.-X.; Sun, J. Tetrahedron 1998, 54, 12445.
13. (d) Sun, X.; Janvier, P.; Zhao, G.; Bienaymé, H.; Zhu. J. Org. Lett. 2001, 3, 877.
14. (e) Janvier, P.; Sun, X.; Bienaymé, H.; Zhu, J. J. Am. Chem. Soc. 2002, 124, 2560.
15. (f) Fayol, A.; Zhu. J. Angew. Chem. Intl. Ed. 2002, 41, 3633.
16. (g) Janvier, P.; Bois-Choussy, M.; Bienaymé, H.; Zhu, J. Angew. Chem. Intl. Ed. Engl. 2003, 42, 811.
17. (h) Wang, Q.; Ganem, B. Tetrahedron Lett. 2003, 44, 6825.
18. Wang, Q.; Ganem, B. Tetrahedron Lett. 2003, 44, 6829.
19. (j) Cuny, G.; Gamez-Montano, R.; Zhu, J. Tetrahedron 2004, 60, 4879.
20. (k) Fayol, A.; Zhu, J. Org. Lett. 2004, 6, 115.
21. Fayol, A.; Zhu, J. Org. Lett. 2005, 7, 239.
22. Tron, G. C.; Zhu, J. Synlett 2005, 532.
23. See, for example: (a) Fayol, A.; Housseman, C.; Sun, X.; Janvier, P.; Bienaymé, H.; Zhu, J. Synthesis 2005, 161.
24. (b) Bossio, R.; Marcaccini, S.; Papaleo, S.; Pepino, R. J. Heterocycl. Chem. 1994, 31, 397.
25. (c) Bossio, R.; Marcaccini, S.; Pellegrino, G.; Pepino, R. Arzneimittelforschung 1992, 42, 1494.
26. (d) Bossio, R.; Marcaccini, S.; Pellegrino, G.; Pepino, R. Farmaco 1992, 47, 1173.
27. (e) Visser, H. G. J.; Nolte, R. J. M.; Zwikker, J. W.; Drenth, W. J. Org. Chem. 1985, 50, 3138.
28. Bossio, R.; Marcaccini, S.; Pepino, R. Liebigs Ann. Chem. 1990, 935.
29. (a) Chupp, J. P.; Leschinsky, K. L. J. Hetercycl. Chem. 1980, 17, 705.
30. (b) Nunami, K.; Suzuki, M.; Hayashi, K. Matsumoto, K.; Yoneda, N.; Takiguchi, K. Agric. Biol. Chem. 1985, 49, 3023.
31. (c) Takiguchi, K.; Yamada, K.; Yamad, K.; Suzuki, M.; Nunami, K.; Hayashi, K.; Matsumoto, K. Agric. Biol. Chem. 1989, 53, 69.
32. Phenyl-substituted isocyanoacetic acid amide can be conventionally synthesized from the corresponding glycine amides via formylation and dehydration.
33. Bleicher, K.; Green, L. G.; Martin, R. E.; Roger-Evans, M. Curr. Opin. Chem. Biol. 2004, 8, 287.
34. Dömling et al. unpublished.
35. The described and other isocyanoamides are commercially available from Synthatex Ltd. (www.synthatex.com).
36. Housseman, C.; Zhu, J. Synlett 2006, 1777.
37. De Luca, L.; Giacomelli, G.; Porcheddu, A. J. Comb. Chem. 2005, 7, 905.
38. (a) Kamijo, S.; Kanazawa, C.; Yamamoto, Y. J. Am. Chem. Soc. 2005, 127, 9260.
39. (b) Sakai, K.; Suzuki, M.; Nunami, K.; Yoneda, N.; Onoda, Y.; Iwasawa, Y. Chem. Pharm. Bull. 1980, 28, 2384.
40. Hwang, S. H.; Olmstead, M. M.; Kurth, M. J. Comb. Chem. 2004, 6, 142.
41. Beck, B.; Larbig, G.; Mejat, B.; Magnin-Lachaux, M.; Picard, A.; Herdtweck, E.; Dömling, A. Org. Lett. 2003, 5, 1047.
42. Gamez M. R.; Zhu, J. Chem. Commun. 2002, 2448.
43. Zhou, X.-T.; Lin, Y.-R.; Dai, L.i-X.; Sun, J. Tetrahedron 1998, 54, 12445.
44. (a) Sawamura, M.; Nakayama, Y.; Kato, T.; Ito, Y. J. Org. Chem. 1995, 60, 1727.
45. (b) Soloshonok, V. A.; Hayashi, T. Tetrahedron Asymmetry 1994, 5, 1091.
46. Chupp, J. P.; Leschinsky, K. L. J. Heterocycl. Chem. 1980, 17, 705.
47. Bossio, R.; Marcaccini, S.; Papaleo, S.; Pepino, R. J. Heterocycl. Chem. 1994, 31, 397.
48. (a) Bossio, R.; Marcaccini, S.; Pepino, R.; Polo, C.; Torroba, T. Anal. Quim. 1991, 87, 93.
49. (b) Bossio, R.; Marcaccini, S.; Paoli, P.; Papaleo, S.; Pepino, R.; Polo, C. Liebigs Ann. Chem. 1991, 843.
50. Yamada, T.; Omote, Y.; Miyazawa, T.; Kuwata, S.; Matsumoto, K. Pept. Chem. 1992, 1991, 367.
51. Bossio, R.; Marcaccini, S.; Pepino, R.; Polo, C.; Torroba, T.; Valle, G. Heterocycles 1989, 29, 1843.
52. Ito, Y.; Sawamura, M.; Hamashima, H.; Emura, T.; Hayashi, T. Tetrahedron Lett. 1989, 30, 4681.
53. Bossio, R.; Marcaccini, S.; Pepino, R.; Polo, C.; Valle, G. Synthesis 1989, 641.
54. Jung, F.; Delvare, C.; Boucherot, D.; Hamon, A. Tetrahedron Lett. 1989, 30, 2375.
55. Ito, Y.; Sawamura, M.; Kobayashi, M.; Hayashi, T. Tetrahedron Lett. 1988, 29, 6321.
56. Schoellkopf, U.; Hausberg, H. H.; Segal, M.; Reiter, U.; Hoppe, I.; Saenger, W.; Lindner, K. Liebigs Ann. Chem. 1981, 439.
57. Nunami, K.; Suzuki, M.; Yoneda, N. J. Org. Chem. 1979, 44, 1887.