A two-stage iterative process for the synthesis of poly-oxazoles

Organic Letters

Volumn 7, Issue 15, 2005, Pages 3351-3354

  Atkins, Jeffery M ^a   Vedejs, Edwin ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

OXAZOLE DERIVATIVE; POLYMER; TELOMESTATIN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; SYNTHESIS;

COMBINATORIAL CHEMISTRY TECHNIQUES; MOLECULAR STRUCTURE; OXAZOLES; POLYMERS;

EID: 23044435339     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051244x     Document Type: Article

References (48)

1. Wipf, P.; Miller, C. P. J. Org. Chem. 1993, 58, 3604.
2. Doyle, K. J.; Moody, C. J. Tetrahedron 1994, 50, 3761.
3. Barrett, A. G. M.; Kohrt, J. T. Synlett 1995, 5, 415.
4. Vedejs, E.; Luchetta, L. M. J. Org. Chem. 1999, 64, 1011.
5. Chattopadhyay, S. K.; Pattenden, G. Synlett 1997, 12, 1342.
6. Liu, P.; Celatka, C. A.; Panek, J. S. Tetrahedron Lett. 1997, 38, 5445.
7. Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 831.
8. Wipf, P.; Methot, J.-L. Org. Lett. 2001, 3, 1261.
9. Celatka, C. A.; Panek, J. S. Tetrahedron Lett. 2002, 43, 7043.
10. Yamada, S.; Shigeno, K.; Kitagawa, K.; Okajima, S.; Asao, T. PCT Int. Appl. WO 2002048153 Al 20020620, 2002; Chem. Abstr. 2002, 137, 47050.
11. Endoh, N.; Tsuboi, K.; Kim, R.; Yonezawa, Y.; Shin, C. Heterocycles 2003, 60, 1567.
12. Coqueron, P.-Y.; Didier, C.; Ciufolini, M. A. Angew. Chem., Int. Ed. 2003, 42, 1411.
13. (a) Nicolaou, K. C.; Bella, M.; Chen, D. Y. K.; Huang, X. H.; Ling, T. T.; Snyder, S. A. Angew. Chem., Int. Ed. 2002, 41, 3495.
14. (b) Nicolaou, K. C.; Rao, P. B.; Hao, J. L.; Reddy, M. V.; Rassias, G.; Huang, X. H.; Chen, D. Y. K.; Snyder, S. A. Angew. Chem., Int. Ed. 2003, 42, 1753.
15. (c) Burgett, A. W. G.; Li, Q.; Wei, Q.; Harran, P. G. Angew. Chem., Int. Ed. 2003, 42, 4961.
16. (d) Magnus, P.; Mciver, E. G. Tetrahedron Lett. 2000, 41, 831.
17. (e) Bagley, M. C.; Hind, S. L.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6897.
18. (a) Shin-ya, K.; Wierzba, K.; Matsuo, K.; Ohtani, T.; Yamada, Y.; Furihata, K.; Hayakawa, Y.; Seto, H. J. Am. Chem. Soc. 2001, 123, 1262.
19. (b) Kim, M.-Y.; Vankayalapati, H.; Shin-ya, K.; Wierzba, K.; Hurley, L. H. J. Am. Chem. Soc. 2002, 124, 2098.
20. Vedejs, E.; Monahan, S. D. J. Org. Chem. 1996, 61, 5192.
21. For coupling with oxazol-2-ylzinc chlorides, see: (a) Anderson, B. A.; Becke, L. M.; Booher, R. N.; Flaugh, M. E.; Harn, N. K.; Kress, T. J.; Varie, D. L.; Wepsiec, J. P. J. Org. Chem. 1997, 62, 8634.
22. (b) Anderson, B. A.; Harn, N. K. Synthesis 1996, 5, 583.
23. For coupling with 2-stanyloxazole, see: (c) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini, P. Synthesis 1987, 8, 693.
24. Hodgetts, K. J.; Kershaw, M. T. Org. Lett. 2003, 5, 2911.
25. (b) Hodgetts, K. J.; Kershaw, M. T. Org. Lett. 2002, 4, 2905.
26. (c) Young, G. L.; Smith, S. A.; Taylor, R. J. K. Tetrahedron Lett. 2004, 45, 3797.
27. (a) Padwa, A.; Cohen, L. A. J. Org. Chem. 1984, 49, 399.
28. (b) Gompper, R.; Effenberger, F. Chem. Ber. 1959, 92, 1928.
29. (c) Yamanaka, H.; Ohba, S.; Sakamoto, T. Heterocycles 1990, 31, 1115.
30. (a) Gompper, R. Chem. Ber. 1956, 89, 1748.
31. (b) Lee, L. F.; Schleppnik, F. M.; Howe, R. K. J. Heterocycl. Chem. 1985, 22, 1621.
32. (c) Haviv, F.; Ratajczyk, J. D.; DeNet, R. W.; Kerdesky, F. A.; Walters, R. L.; Schmidt, S. P.; Holms, J. H.; Young, P. R.; Carter, G. W. J. Med. Chem. 1988, 31, 1719.
33. Hilf, C.; Bosold, F.; Harms, K.; Marsch, M.; Boche, G. Chem. Ber. 1997, 130, 1213.
34. 4 or trichloroacetyl chloride have been reported as electrophilic chlorine sources to generate 2-chlorothiazole via halogen-metal exchange. See: (a) Boga, C.; Del Vecchio, E.; Forlani, L.; Todesco, P. E. J. Organomet. Chem. 2000, 601, 233.
35. (b) Boga, C.; Del Vecchio, E.; Forlani, L.; Milanesi, L.; Todesco, P. E. J. Organomet. Chem. 1999, 588, 155.
36. (a) Chinchilla, R.; Najera, C.; Yus, M. Chem. Rev. 2004, 104, 2667.
37. (b) Schroeder, R.; Schoellkopf, U.; Blume, E.; Hoppe, I. Justus Liebigs Ann. Chem. 1975, 3, 533.
38. (c) Jacobi, P. A.; Ueng, S.; Carr, D. J. Org. Chem. 1979, 44, 2042.
39. (d) Hodges, J. C.; Patt, W. C.; Connolly, C. J. J. Org. Chem. 1991, 56, 449.
40. (e) Whitney, S. E.; Rickborn, B. J. Org. Chem 1991, 56, 3058.
41. For reviews of TosMIC and α-metalated isocyanides, see: (a) van Leusen, A. M.; van Leusen, D. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: New York, 1995; Vol. 7, p 4973.
42. (b) Schöllkopf, U. Angew. Chem., Int. Ed. Engl. 1977, 16, 339.
43. (c) Tandon, V. K.; Rai, S. Sulfur Rep. 2003, 24, 307.
44. (d) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3169.
45. (e) Hoppe, D. Angew. Chem., Int. Ed. Engl. 1974, 13, 789.
46. (f) Marcaccini, S.; Torroba, T. Org. Prep. Proced. Int. 1993, 25, 141.
47. Sisko, J.; Kassick, A. J.; Mellinger, M.; Filan, J. J.; Allen, A.; Olsen, M. A. J. Org. Chem. 2000, 65, 1516.
48. A half-life of ca. 15 min has been reported for TosMIC and NaH/DME. (van Leusen, A. M.; Wildeman, J.; Oldenziel, O. H. J. Org. Chem. 1977, 42, 1153.) We have found that TosMIC anion is substantially more stable in DMF as the solvent.