Gold catalysis: Mild conditions for the synthesis of oxazoles from N-propargylcarboxamides and mechanistic aspects

Organic Letters

Volumn 6, Issue 23, 2004, Pages 4391-4394

  Hashmi, A Stephen K ^a   Weyrauch, Jan P ^a   Frey, Wolfgang ^a   Bats, Jan W ^b  

^a UNIVERSITY OF STUTTGART   (Germany)

^b GOETHE UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDINE; GOLD; OXAZOLE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 9444284312     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0480067     Document Type: Article

References (28)

1. (a) Palmer, D. C.; Venkatraman, S. In The Chemistry of Heterocyclic Compounds, A Series of Monographs, Oxazoles: Synthesis, Reactions, and Spectroscopy, Part A; Palmer, D. C., Ed.; John Wiley & Sons: Hoboken, NJ, 2003.
2. (b) Lang-Fugmann, S. In Methoden der Organischen Chemie (Houben-Weyl), Band E8a Hetarene III/Teil 1; Schaumann, E., Ed.; Georg Thieme Verlag: Stuttgart, 1993.
3. (c) Lakham, R.; Ternai, B. Adv. Heterocycl. Chem. 1974, 17, 99.
4. (d) Pattenden, G. J. Heterocycl. Chem. 1992, 29, 607.
5. (a) Nilsson, B. M.; Hacksell, U. J. Heterocycl. Chem. 1989, 26, 269.
6. (b) Nilsson, B. M.; Vargas, H. M.; Ringdahl, B.; Hacksell, U. J. Med. Chem. 1992, 35, 285.
7. (a) Freedman, J.; Huber, E. W. J. Heterocycl. Chem. 1990, 72, 4, 343.
8. (b) Reisch, J.; Usifoh, C. O.; Okoh, E.; Oluwadiya, J. O. Pharmazie 1992, 47, 18.
9. See also: (c) Usifoh, C. O.; Edema, M. O. S. Afr. J. Chem. 2000, 53, 47. (d) Clark, D.; Travis, D. A. Bioorg. Med. Chem. 2001, 9, 2857.
10. See also: (c) Usifoh, C. O.; Edema, M. O. S. Afr. J. Chem. 2000, 53, 47. (d) Clark, D.; Travis, D. A. Bioorg. Med. Chem. 2001, 9, 2857.
11. (a) Schulte, K. E. et al. Arch. Pharm. Ber. Dtsch. Pharm. Ges. 1966, 299, 107.
12. (b) Eloy, F.; Deryckere, A. Chim. Ther. 1973, 8, 437.
13. (c) Street, L. J.; Baker, R.; Castro, J. L.; Chambers, M. S.; Guiblin, A. R.; Hobbs, S. C.; Matassa, V. G.; Reeve, A. J.; Beer, M. S. J. Med. Chem. 1993, 36, 1529.
14. Amiet, G.; Hügel, H. M.; Nurlawis, F. Synlett 2002, 495.
15. Arcadi, A.; Cacchi, S.; Cascia, L.; Fabrizi, G.: Marinelli, F. Org. Lett. 2001, 3, 2501.
16. Bacchi, A.; Costa, M.; Gabriele, B.; Pelizzi, G.; Salerno, G. J. Org. Chem. 2002, 67, 4450.
17. Hashmi, A. S. K. Gold Bull. 2003, 36, 3.
18. (a) Tiecco, M.; Testaferri, L.; Tingoli, M.; Marini, F. J. Org. Chem. 1993, 58, 1349.
19. (b) Capozzi, G.; Caristi, C.; Gattuso, M.; d'Alcontres, G. S. Tetrahedron Lett. 1981, 22, 3325.
20. (c) Capozzi, G.; Caristi, C.; Gattuso, M. J. Chem. Soc., Perkin Trans. 1 1984, 255.
21. (d) Kennedy-Smith, J. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 4526.
22. (a) Reisch, J.; Usifoh, C. O.; Oluwadiya, J. O. J. Heterocycl. Chem. 1989, 26, 1495.
23. (b) Fráter, Gy. Tetrahedron Lett. 1976, 49, 4517.
24. Teles, J. H.; Brode, S.; Chabanas, M. Angew. Chem. 1998, 110, 1475; Angew. Chem., Int. Ed., 1998, 37, 1415.
25. Teles, J. H.; Brode, S.; Chabanas, M. Angew. Chem. 1998, 110, 1475; Angew. Chem., Int. Ed., 1998, 37, 1415.
26. (a) Schlossarcyk, H.; Sieber, W.; Hesse, M.; Hansen, H.-J.; Schmid, H. Helv. Chim. Acta 1973, 56, 875.
27. (b) Oelberg, D. G.; Schiavelli, M. D. J. Org. Chem. 1977, 42, 1804.
28. (c) Shigemasa, Y.; Yasui, M.; Ohari, S.-i.; Sasaki, M.; Sashiwa, H.; Saimoto, H. J. Org. Chem. 1991, 56, 910.