Efficient synthesis of substituted indoles and benzazoles by oxidative aromatization using activated carbon-Molecular oxygen system

Heterocycles

Volumn 74, Issue C, 2007, Pages 629-635

  Nomura, Yukiko ^a   Kawashita, Yuka ^a   Hayashi, Masahiko ^a  

^a KOBE UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 40749083198     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (51)

1. Gilchrist T.L. Heterocyclic Chemistry. third edition (1997), Longman Chapter 6
2. Katritzky A.R., and Pozharskii A.F. Handbook of Heterocyclic Chemistry. second edition (2000), Pergamon Chapter 4.4.
3. Eicher T., and Hauptmann S. The Chemistry of Heterocycles (2003), Wiley-VCH Chapter 5
4. In: Li J.J. (Ed). Name Reactions in Heterocyclic Chemistry (2005), John Wiley & Sons Chapter 3
5. Fischer E., and Jourdan F. Ber. 16 (1883) 2241
6. Fischer E., and Hess O. Ber. 17 (1884) 559
7. Robinson B. Chem. Rev. 69 (1969) 227
8. Robinson B. The Fischer Indole Synthesis (1982), John Wiley & Sons 923
9. Huge D.L. Org. Prep. Proced. Int. 25 (1993) 607
10. Miller B., and Matjeka E.R. Tetrahedron Lett. (1977) 131
11. Chen C.-y., Senanayake C.H., Bill T.J., Larsen R.D., Verhoeven T.R., and Reider P.J. J. Org. Chem. 59 (1994) 3738
12. Hughes D.L., and Zhao D. J. Org. Chem. 58 (1993) 228
13. Fujii H., Mizusuna A., Tanimura R., and Nagase H. Heterocycles 45 (1997) 2109
14. Reissert A. Ber. 30 (1897) 1030
15. Gassman P.G., van Bergen T.J., Gilbert D.P., and Cue B.W. J. Am. Chem. Soc. 96 (1974) 5495
16. Bartoli G., Palmieri G., Bosco M., and Dalpozzo R. Tetrahedron Lett. 30 (1989) 2129
17. Bosco M., Dalpozzo R., Bartoli G., Palmieri G., and Petrini M. J. Chem. Soc., Perkin Trans 2 (1991) 657
18. Bartoli G., Bosco M., Dalpozzo R., Palmieri G., and Marcantoni E. J. Chem. Soc., Perkin Trans 1 (1991) 2757
19. Bartoli G. Acc. Chem. Res. 17 (1984) 109 See also
20. Dobbs A. J. Org. Chem. 66 (2001) 638
21. Madelung W. Ber. 45 (1912) 1128
22. See also,. Houlihan W.J., Parrino V.A., and Uike Y. J. Org. Chem. 46 (1981) 4511
23. Miyashita K., Tsuchiya K., Kondoh K., Miyabe H., and Imanishi T. Heterocycles 42 (1996) 513
24. Miyashita K., Kondoh K., Tsuchiya K., Miyabe H., and Imanishi T. J. Chem. Soc., Perkin Trans 1 (1996) 1261
25. Hughes I. Tetrahedron Lett. 37 (1996) 7595
26. Nenitzescu C.D. Bull. Soc. Chim. Romania 11 (1929) 37
27. See also,. Adams R., and Samuels Jr. W.P. J. Am. Chem. Soc. 77 (1955) 5375
28. Parker K.A., and Kang S.-K. J. Org. Chem. 44 (1979) 1536
29. Larock R.C., and Yum E.K. J. Am. Chem. Soc. 113 (1991) 6689
30. Larock R.C. Pure Appl. Chem. 71 (1999) 1435
31. Larock R.C. J. Organomet. Chem. 576 (1999) 114
32. Roesch K.R., and Larock R.C. J. Org. Chem. 66 (2001) 412
33. Hara T., Mori K., Mizugaki T., Ebitani K., and Kaneda K. Tetrahedron Lett. 44 (2003) 6207
34. Nakamichi N., Kawashita Y., and Hayashi M. Org. Lett. 4 (2002) 3955
35. Nakamichi N., Kawashita Y., and Hayashi M. Synthesis (2004) 1015
36. Hayashi M., and Kawashita Y. Lett. Org. Lett. 3 (2006) 571
37. Nakamichi N., Kawabata H., and Hayashi M. J. Org. Chem. 68 (2003) 8272
38. Kawashita Y., Nakamichi N., Kawabata H., and Hayashi M. Org. Lett. 5 (2003) 3713
39. Kawashita Y., Ueba C., and Hayashi M. Tetrahedron Lett. 47 (2006) 4231
40. Bellina F., Cauteruccio S., and Rossi R. Eur. J. Org. Chem. (2006) 1379
41. Previously reported synthesis of benzazoles. For benzimidazole:. Kočcevar M., Sušin P., and Polanc S. Synthesis (1993) 773
42. Lam P.Y.S., Vincent G., Bonne D., and Clark C.G. Tetrahedron Lett. 44 (2003) 4927
43. For benzothiazole:. Davis C.S., Knevel A.M., and Jenkins G.L. J. Org. Chem. 27 (1962) 1919
44. Itoh T., Nagata K., Miyazaki M., and Ohsawa A. Heterocycles 52 (2000) 1037
45. For benzoxazole:. El-Sheikh M.I., Marks A., and Biehl E.R. J. Org. Chem. 46 (1981) 3256
46. Haley M.F., and Yates K. J. Org. Chem. 52 (1987) 1825
47. See also,. Grundmann C., and Kreutzberger A. J. Am. Chem. Soc. 77 (1955) 6559
48. Cadogan J.I.G., Hickson C.L., and McNab H. J. Chem. Soc., Perkin Trans 1 (1985) 1885
49. Singh H., and Sarin R. Tetrahedron 42 (1986) 1449
50. Frachey G., Crestini C., Bernini R., Saladino R., and Mincione E. Heterocycles 38 (1994) 2621
51. Brown G.R., and Foubister A.J. Synthesis (1982) 1036