Intramolecular Pd(II)-catalyzed cyclization of propargylamides: Straightforward synthesis of 5-oxazolecarbaldehydes

Journal of Organic Chemistry

Volumn 73, Issue 12, 2008, Pages 4746-4749

  Beccalli, Egle M ^a   Borsini, Elena ^b   Broggini, Gianluigi ^b   Palmisano, Giovanni ^b   Sottocornola, Silvia ^b  

^a UNIVERSITY OF MILAN   (Italy)

^b UNIVERSITY OF INSUBRIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS; COMPUTER NETWORKS; NETWORK PROTOCOLS; PALLADIUM; PALLADIUM COMPOUNDS;

(E ,3E) PROCESS; AMERICAN CHEMICAL SOCIETY (ACS); CATALYTIC AMOUNTS; CHEMICAL EQUATIONS; DIRECT SYNTHESIS; FORMYLATION; HETEROCYCLIZATION; INTRA-MOLECULAR REACTIONS; OXAZOLE; SYNTHESIS (OF CHIRAL IONIC LIQUIDS); SYNTHETIC PATHWAYS; WIDE-RANGE;

SYNTHESIS (CHEMICAL);

5 OXAZOLECARBALDEHYDE DERIVATIVE; AMIDE; OXAZOLE DERIVATIVE; PALLADIUM; PROPARGYLAMIDE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; STEREOCHEMISTRY; STEREOISOMERISM; STEREOSPECIFICITY; STOICHIOMETRY; SYNTHESIS;

ALDEHYDES; AMIDES; CATALYSIS; CYCLIZATION; MAGNETIC RESONANCE SPECTROSCOPY; OXAZOLES; PALLADIUM; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 45249091683     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800621n     Document Type: Article

References (49)

1. (a) Li, J. J.; Gribble G. W. Palladium in Heterocyclic Chemistry - A Guide for the Synthetic Chemist, 2nd ed.; Elsevier: Amsterdam, The Netherlands, 2007.
2. (b) Zeni, G.; Larock, R. C. Chem. Rev. 2004, 104, 2285.
3. (c) Zeni, G.; Larock, R. C. Chem. Rev. 2006, 106, 4644.
4. Tsuji, J. Palladium Reagents and Catalysts: New Perspectives for the 21 st Century; Wiley and Sons: New York, 2003.
5. (a) Stahl, S. S. Angew. Chem., Int. Ed. 2004, 43, 3400.
6. (b) Sigman, M. S.; Schultz, M. J. Org. Biomol. Chem. 2004, 2, 2551.
7. (c) Beccalli, E. M.; Broggini, G.; Martinelli, M.; Sottocornola, S. Chem. Rev. 2007, 107, 5318.
8. (a) Zhang, Z.; Tan, J.; Wang, Z. Org. Lett. 2008, 10, 173.
9. (b) Muñiz, K.; Hövelmann, C. H.; Streuff, J. J. Am. Chem. Soc. 2008, 130, 763.
10. (c) Popp, B. V.; Wendlandt, J. E.; Landis, C. R.; Stahl, S. S. Angew. Chem., Int. Ed. 2007, 46, 601.
11. (d) Yang, S.; Li, B.; Wan, X.; Shi, Z. J. Am. Chem. Soc. 2007, 129, 6066.
12. (e) Liu, G.; Stahl, S. S. J. Am. Chem. Soc. 2007, 129, 6328.
13. (f) Thiery, E.; Chevrin, C.; Le Bras, J.; Harakat, D.; Muzart, J. J. Org. Chem. 2007, 72, 1859.
14. (g) Penn, L.; Shpruhman, A.; Gelman, D. J. Org. Chem. 2007, 72, 3875.
15. (h) Beniazza, R.; Dunet, J.; Robert, F.; Schenk, K.; Landais, Y. Org. Lett. 2007, 9, 3913.
16. (i) Piera, J.; Persson, A.; Caldentey, X.; Bäckvall, J.-E. J. Am. Chem. Soc. 2007, 129, 14120.
17. (j) Rogers, M. M.; Kotov, V.; Chatwichien, J.; Stahl, S. S. Org. Lett. 2007, 9, 4331.
18. (k) Zhang, Z.; Pan, J.; Wang, Z. Chem. Comm. 2007, 4686.
19. (l) Devalina, R.; Sunanda, P.; Sulagna, B.; Jayanta, K. R. Tetrahedron Lett. 2007, 48, 8005.
20. (m) Lindh, J.; Enquist, P.-A.; Pilotti, A.; Nilsson, P.; Larhed, M. J. Org. Chem. 2007, 72, 7957.
21. (a) Beccalli, E. M.; Broggini, G. Tetrahedron Lett. 2003, 44, 1919.
22. (b) Abbiati, G.; Beccalli, E. M.; Broggini, G.; Zoni, C. J. Org. Chem. 2003, 68, 7625.
23. (c) Beccalli, E. M.; Broggini, G.; Paladino, G.; Penoni, A.; Zoni, C. J. Org. Chem. 2004, 69, 5627.
24. (d) Beccalli, E. M.; Broggini, G.; Martinelli, M.; Paladino, G. Tetrahedron 2005, 61, 1077.
25. (e) Abbiati, G.; Beccalli, E. M.; Broggini, G.; Martinelli, M.; Paladino, G. Synlett 2006, 73.
26. (a) Kato, Y.; Fusetani, N.; Matsunaga, S.; Hashimoto, K.; Fujita, S.; Furuya, T. J. Am. Chem. Soc. 1986, 108, 2780.
27. (b) Maryanoff, C. A. In Heterocyclic Compounds; Turchi, I. J., Ed.; Wiley & Sons: New York, 1986; Vol. 45, Chapter 5.
28. (c) Carmeli, S.; Moore, R. E.; Patterson, G. M.; Cortbett, T. H.; Valeriote, F. A. J. Am. Chem. Soc. 1990, 112, 8195.
29. (d) Pattenden, G. J. Heterocycl. Chem. 1992, 29, 607.
30. (e) Lewis, J. R. Nat. Prod. Rep. 1995, 12, 135.
31. (f) Anderson, B. A.; Becke, L. M.; Booher, R. N.; Flaugh, M. E.; Harnh, N. K.; Kress, D. L.; Wepsiec, J. P. J. Org. Chem. 1997, 62, 8634.
32. (g) Palmer, D. C.; Venkatraman, S. In The Chemistry of Heterocycles Compounds, A Series of Monographs, Oxazoles: Synthesis, Reactions and Spettroscopy, Part A; Palmer, D.C. Ed.; John Wiley & Sons: Hoboken, NJ, 2003.
33. (a) Schulte, K. E.; Reisch, J.; Sommer, M. Arch. Pharm. 1966, 107.
34. (b) Eloy, F.; Deryckere, A. Chim. Thér. 1973, 437.
35. (c) Nilsson, B. M.; Hacksell, U. J. Heterocycl. Chem. 1989, 26, 269.
36. (d) Freedman, J.; Huber, E. W. J. Heterocycl. Chem. 1990, 27, 343.
37. (e) Wipf, P.; Rahman, L. T.; Rector, S. R. J. Org. Chem. 1998, 63, 7132.
38. (f) Clark, D. C.; Travis, D. A. Bioorg. Med. Chem. 2001, 9, 2857.
39. (g) Arcadi, A.; Cacchi, S.; Cascia, L.; Fabrizi, G.; Marinelli, F. Org. Lett. 2001, 3, 2501.
40. (h) Bacchi, A.; Costa, M.; Gabriele, B.; Pelizzi, G.; Salerno, G. J. Org. Chem. 2002, 67, 4450.
41. (i) Hashmi, A. S. K.; Weyrauch, J. P.; Frey, W.; Bats, J. W. Org. Lett. 2004, 6, 4391.
42. Kumar, D.; Sundaree, S.; Patel, G.; Rao, V. S. Tetrahedron Lett. 2008, 49, 867.
43. (a) Street, L. J.; Sternfeld, F.; Jelley, R. A.; Reeve, A. J.; Carling, R. W.; Moore, K. W.; McKernan, R. M.; Sohal, B.; Cook, S.; Pike, A.; Dawson, G. R.; Bromidge, F. A.; Wafford, K. A.; Seabrook, G. R.; Thompson, S. A.; Marshall, G.; Pillai, G. V.; Castro, J. L.; Atack, J. R.; MacLeod, A. M. J. Med. Chem. 2004, 47, 3642.
44. (b) Wipf, P.; Reeves, J. T.; Balachandran, R.; Day, B. W. J. Med. Chem. 2002, 45, 1901.
45. (c) Meyers, A. I.; Tavares, F. X. J. Org. Chem. 1996, 61, 8207.
46. (d) Shimano, M.; Meyers, A. I. Tetrahedron Lett. 1997, 38, 5415.
47. (e) Meyers, A. I.; Tavares, F. X. Tetrahedron Lett. 1994, 35, 2481.
48. (f) Barrish, J. C.; Singh, J.; Spergel, S. H.; Han, W. C.; Kissick, T. P.; Kronenthal, D. R.; Mueller, R. H. J. Org. Chem. 1993, 58, 4494.
49. McNulty, P. J.; Swithenbank, C.; Viste, K. L.; Von Meyer, W. C. Ger. Offen. DE 2025961 19710114, 1971. Chem. Abstr. 1971, 74, 75602.