A silver-mediated one-step synthesis of oxazoles

Journal of Organic Chemistry

Volumn 76, Issue 9, 2011, Pages 3519-3522

  Ritson, Dougal J ^a   Spiteri, Christian ^a   Moses, John E ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ONE STEP SYNTHESIS; OXAZOLES;

SILVER;

OXAZOLE; SILVER;

ARTICLE; CHEMICAL STRUCTURE; COMPLEX FORMATION; ONE POT SYNTHESIS; REACTION ANALYSIS;

CATALYSIS; GREEN CHEMISTRY TECHNOLOGY; OXAZOLES; SILVER;

EID: 79955566686     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1025332     Document Type: Article

References (45)

1. Palmer, D. C.; Taylor, E. C. The Chemistry of Heterocyclic Compounds. Oxazoles: Synthesis, Reactions and Spectroscopy, Parts A & B; Wiley: Hoboken, NJ, 2004; Vol. 60.
2. Yeh, V. S. C. Tetrahedron 2004, 60, 11995-12042
3. For a review see: Grant, T. G.; Meyers, A. I. Tetrahedron 1994, 50, 2297-2360
4. Graham, T. H. Org. Lett. 2010, 12, 3614-3617
5. Murai, K.; Takahara, Y.; Matsushita, T.; Komatsu, H.; Fujioka, H. Org. Lett. 2010, 12, 3456-3459
6. Sakakura, A.; Kondo, R.; Ishihara, K. Org. Lett. 2005, 7, 1971-1974
7. Davies, J. R.; Kane, P. D.; Moody, C. J. Tetrahedron 2004, 60, 3967-3977
8. Kreisberg, J. D.; Magnus, P.; Shinde, S. Tetrahedron Lett. 2002, 43, 7393-7396
9. Brain, C. T.; Paul, J. M. Synlett 1999, 1642-1644
10. Meyers, A. I.; Tavares, F. X. J. Org. Chem. 1996, 61, 8207-8215
11. Shapiro, R. J. Org. Chem. 1993, 58, 5759-5764
12. Wan, C.; Zhang, J.; Wang, S.; Fan, J.; Wang, Z. Org. Lett. 2010, 12, 2338-2341
13. Shi, B.; Blake, A. J.; Lewis, W.; Campbell, I. B.; Judkins, B. D.; Moody, C. J. J. Org. Chem. 2010, 75, 152-161
14. dos Santos, A.; El Kaïm, L.; Grimaud, L.; Ronsseray, C. Chem. Commun. 2009, 3907-3909
15. Bonne, D.; Dekhane, M.; Zhu, J. Angew. Chem., Int. Ed. 2007, 46, 2485-2488
16. Kumar, M. P.; Liu, R.-S. J. Org. Chem. 2006, 71, 4951-4955
17. Merkul, E.; Müller, T. J. J. Chem. Commun. 2006, 4817-4819
18. Barrett, A. G. M.; Cramp, S. M.; Hennessy, A. J.; Procopiou, P. A.; Roberts, R. S. Org. Lett. 2001, 3, 271-273
19. Lechel, T.; Lentz, D.; Reissig, H.-U. Chem. - Eur. J. 2009, 15, 5432-5435
20. Kison, C.; Opatz, T. Chem. - Eur. J. 2009, 15, 843-845
21. Araki, H.; Katoh, T.; Inoue, M. Tetrahedron Lett. 2007, 48, 3713-3717
22. Keni, M.; Tepe, J. J. J. Org. Chem. 2005, 70, 4211-4213
23. Wipf, P.; Aoyama, Y.; Benedum, T. E. Org. Lett. 2004, 6, 3593-3595.
24. Coqueron, P.-Y.; Didier, C.; Ciufolini, M. A. Angew. Chem., Int. Ed. 2003, 42, 1411-1414
25. Wipf, P.; Methot, J.-L. Org. Lett. 2001, 3, 1261-1264
26. Eastwood, F. W.; Perlmutter, P.; Yang, Q. J. Chem. Soc., Perkin Trans. 1 1997, 35-42
27. Ang, K. H.; Prager, R. H.; Smith, J. A.; Weber, B.; Williams, C. M. Tetrahedron Lett. 1996, 37, 675-678
28. Yoo, S.-K. Tetrahedron Lett. 1992, 33, 2159-2162
29. Robinson, R. J. Chem. Soc., Trans. 1909, 95, 2167-2174
30. Gabriel, S. Ber. 1910, 43, 134-138
31. Wipf, P.; Miller, C. P. J. Org. Chem. 1993, 56, 3604-3606
32. For leading references see: Philips, A. J.; Uto, Y.; Wipf, P.; Reno, M. J.; Williams, D. R. Org. Lett. 2000, 2, 1165-1168
33. Jiang, H.; Huang, H.; Cao, H.; Qi, C. Org. Lett. 2010, 12, 5561-5563
34. Blümlein, F. O. Ber. 1884, 17, 2578-2581
35. Lewy, M. Ber. 1887, 20, 2576-2580
36. Moody., C. J.; Swann., E. J. Med. Chem. 1995, 38, 1039-1043
37. Panek, J. S.; Beresis, R. T. J. Org. Chem. 1996, 61, 6496-6497
38. Ramón, R. S.; Bosson, J.; Díez-Gonzàlez, S.; Marion, N.; Nolan, S. P. J. Org. Chem. 2010, 75, 1197-1202
39. Many silver salts are comparable in price to DAST, for example. AgBr can be recovered by simple filtration and recycled.
40. 2 (δ 6.10) of 1. Other by-products were negligible.
41. 4, e.g., when the reaction time was decreased to 1 h the yield dropped to 76%, when THF was used as solvent only 19% of 3 was recovered.
42. Aguilar, E.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 2473-2476
43. Holzapfel, C. W.; Pettit, G. R. J. Org. Chem. 1985, 50, 2323-2327
44. Cheung, C.-M.; Goldberg, F. W.; Magnus, P.; Russell, C. J.; Turnbull, R.; Vince Lynch, V. J. Am. Chem. Soc. 2007, 129, 12320-12327
45. Doi, T.; Yoshida, M.; Shin-ya, K.; Takahashi, T. Org. Lett. 2006, 8, 4165-4167