Synthesis of oxazoles through Pd-catalyzed cycloisomerization-allylation of N-propargylamides with allyl carbonates

Tetrahedron Letters

Volumn 51, Issue 11, 2010, Pages 1471-1474

  Saito, Akio ^a   Iimura, Koichi ^a   Hanzawa, Yuji ^a  

^a SHOWA PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BIS(2,6 DIISOPROPYLPHENYL)IMIDAZOL 2 YLIDENE; AMIDE; CARBONIC ACID; IMIDAZOLE DERIVATIVE; OXAZOLE DERIVATIVE; PALLADIUM COMPLEX; PROPARGYLAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ISOMERIZATION;

EID: 75749124294     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.01.018     Document Type: Article

References (68)

1. Alonso F., Beletskaya I.P., and Yus M. Chem. Rev. 104 (2004) 3079
2. Nakamura I., and Yamamoto Y. Chem. Rev. 104 (2004) 2127
3. Kirsch S.F. Synthesis (2008) 3183
4. Zeni G., and Larock R.C. Chem. Rev. 104 (2004) 2285
5. Zeni G., and Larock R.C. Chem. Rev. 106 (2006) 4644
6. Tsuji J. Palladium Reagents and Catalysts: New Perspectives for the 21st Century (2003), Wiley and Sons, New York
7. Li J.J., and Gribble G.W. Palladium in Heterocyclic Chemistry - A Guide for the Synthetic Chemist. second ed. (2007), Elsevier, Amsterdam, The Netherlands
8. For recent examples:. Arcadi A., Cacchi S., Fabrizi G., Marinelli F., and Parisi L.M. Tetrahedron 59 (2003) 4661
9. Cacchi S., Fabrizi G., and Moro L. J. Org. Chem. 62 (1997) 5327
10. Arcadi A., Burini A., Cacchi S., Delmastro M., Marinelli F., and Pietroni B.R. J. Org. Chem. 57 (1992) 976
11. Hu Y., Nawoschik K.J., Liao Y., Ma J., Fathi R., and Yang Z. J. Org. Chem. 69 (2004) 2235
12. Cacchi S., Fabrizi G., Marinelli F., Moro L., and Pace P. Synlett (1997) 1363
13. Wolf L.B., Tjen K.C.M.F., Rutjes F.P.J.T., Hiemstra H., and Schoemaker H.E. Tetrahedron Lett. 39 (1998) 5081
14. Arcadi A. Synlett (1997) 941
15. Bouyssi D.B., Cavicchioli M., and Balme G. Synlett (1997) 944
16. Chowdhury C., Chaudhuri G., Guha S., Mukherjee A.K., and Kundu N.G. J. Org. Chem. 63 (1998) 1863
17. Mukhopadhyay R., and Kundu N.G. Synlett (2001) 1143
18. Luo F.-T., Schreuder I., and Wang R.-T. J. Org. Chem. 57 (1992) 2213
19. Luo F.-T., and Wang R.-T. Tetrahedron Lett. 33 (1992) 6835
20. For recent examples:. Gabriele B., Salerno G., De Pascali F., Costa M., and Chiusoli G.P. J. Organomet. Chem. 593-594 (2000) 409
21. Marshall J.A., and Yanik M.M. Tetrahedron Lett. 41 (2000) 4717
22. Kato K., Nishimura A., Yamamoto Y., and Akita H. Tetrahedron Lett. 42 (2001) 4203
23. Kato K., Yamamoto Y., and Akita H. Tetrahedron Lett. 43 (2002) 4915
24. Arcadi A., and Rossi E. Tetrahedron Lett. 37 (1996) 6811
25. Okuro K., Furuune M., Miura M., and Nomura M. J. Org. Chem. 57 (1992) 4754
26. Copéret C., Sugihara T., Wu G., Shimoyama I., and Negishi E. J. Am. Chem. Soc. 117 (1995) 3422
27. Hu Y., Zhang Y., Yang Z., and Fathi R. J. Org. Chem. 67 (2002) 2365
28. Arcadi A., Cacchi S., Carnicelli V., and Marinelli F. Tetrahedron 50 (1994) 437
29. Yanagihara N., Lambert C., Iritani K., Utimoto K., and Nozaki H. J. Am. Chem. Soc. 108 (1986) 2753
30. Tsuda T., Ohashi Y., Nagahama N., Sumiya R., and Saegusa T. J. Org. Chem. 53 (1988) 2650
31. Cacchi S., Fabrizi G., and Moro L. Synlett (1998) 741
32. Cacchi S., Fabrizi G., and Pace P. J. Org. Chem. 63 (1998) 1001
33. Uemura K., Kawaguchi T., Takayama H., Nakamura A., and Inoue Y. J. Mol. Catal. A: Chem. 139 (1999) 1
34. Nakamura H., Ohtaka M., and Yamamoto Y. Tetrahedron Lett. 43 (2002) 7631
35. Turchi I.J., and Dewar M.J.S. Chem. Rev. 75 (1975) 389
36. Wasserman H.H., McCarthy K.E., and Prowse K.S. Chem. Rev. 75 (1986) 845
37. Wipf P. Chem. Rev. 95 (1995) 2115
38. Jin Z. Nat. Prod. Rep. 20 (2003) 584
39. Jin Z. Nat. Prod. Rep. 26 (2009) 382
40. In: Palmer D.C. (Ed). Oxazoles: Synthesis, Reactions, and Spectroscopy, Part A vol. 60 (2003), J. Wiley & Sons, Hoboken, NJ
41. In: Palmer D.C. (Ed). Oxazoles: Synthesis, Reactions, and Spectroscopy, Part B vol. 60 (2004), J. Wiley & Sons, Hoboken, NJ
42. Dalvie D.K., Kalgutkar A.S., Khojasteh-Bakht S.C., Obach R.S., and O'Donnell J.P. Chem. Res. Toxicol. 15 (2002) 269
43. McGovern S.L., Caselli E., Grigorieff N., and Shoichet B.K. J. Med. Chem. 45 (2002) 1712
44. Murcia-Soler M., Perez-Gimenez F., Garcia-March F.J., Salabert-Salvador M.T., Diaz-Villanueva W., Castro-Bleda M.J., and Villanueva-Pareja A. J. Chem. Inf. Comput. Sci. 44 (2004) 1031
45. For recent examples:. Xia M. J. Chem. Res. (2000) 382
46. Milton M.D., Inada Y., Nishibayashi Y., and Uemura S. Chem. Commun. (2004) 2712
47. Hashmi A.S.K., Rudolph M., Schymura S., Visus J., and Frey W. Eur. J. Org. Chem. (2006) 4905
48. Ueda S., and Nagasawa H. Angew. Chem., Int. Ed. 47 (2008) 6411
49. Xia Q., and Ganem B. Org. Lett. 4 (2002) 1631
50. Mihara H., Xu Y., Shepherd E., Matsunaga S., and Shibasaki M. J. Am. Chem. Soc. 131 (2009) 8384
51. Arcadi A., Cacchi S., Cascia L., Fabrizi G., and Marinelli F. Org. Lett. 3 (2001) 2501
52. Merkul E., and Müller T.J.J. Chem. Commun. (2006) 4817
53. Bacchi A., Costa M., Gabriele B., Pelizzi G., and Salerno G. J. Org. Chem. 67 (2002) 4450
54. Beccalli E.M., Borsini E., Broggini G., Palmisano G., and Sottocornola S. J. Org. Chem. 73 (2008) 4746
55. Hashmi A.S.K., Weyrauch J.P., Frey W., and Bats J.W. Org. Lett. 6 (2004) 4391
56. Base-promoted cycloisomerization:. Eloy F., and Deryckere A. Chim. Ther. (1973) 437
57. Nilsson B.M., and Hacksell U. J. Heterocycl. Chem. 26 (1989) 269
58. Freedman J., and Huber E.W. J. Heterocycl. Chem. 27 (1990) 343
59. Wipf P., Rahman L.T., and Rector S.R. J. Org. Chem. 63 (1998) 7132
60. Clark D.C., and Travis D.A. Bioorg. Med. Chem. 9 (2001) 2857
61. See:. Wipf P., Aoyama Y., and Benedum T.E. Org. Lett. 20 (2004) 3593
62. 3 (3 equiv) in the absence of allyl ethyl carbonate gave 3a in 89% yield, the base-promoted reaction might be involved in the formation of 3a in the present synthetic method of 2a.
63. For review:. Kantchev E.A.B., O'Brien C.J., and Organ M.G. Angew. Chem., Int. Ed. 46 (2007) 2768
64. For examples of Tsuji-Trost reaction:. Sato Y., Yoshino T., and Mori M. Org. Lett. 5 (2003) 31
65. Sato Y., Yoshino T., and Mori M. J. Organomet. Chem. 690 (2005) 5753
66. 3P):. Fantasia S., and Nolan S.P. Chem. Eur. J. 14 (2008) 6987
67. Preparation of (IPr)Pd(allyl)Cl:. Normand A.T., Stasch A., Ooi L.-L., and Cavell K.J. Organometallics 27 (2008) 6507
68. Although the Pd-catalyzed formation of 3-allylated indoles from o-alkynyl-trifluoroacetanilides and allylation reagents was reported to proceed via N-allyl-o-alkynyl-trifluoroacetanilide intermediates, N-allyl-N-(prop-2-ynyl)benzamide was not converted into the oxazole 2a by the present catalytic system. See, Ref. 5c.