Efficient synthesis of indoles using [3,3]-sigmatropic rearrangement of N-trifluoroacetyl enehydrazines

Tetrahedron

Volumn 62, Issue 15, 2006, Pages 3629-3647

  Miyata, Okiko ^a   Takeda, Norihiko ^a   Kimura, Yasuo ^a   Takemoto, Yoshiji ^b   Tohnai, Norimitsu ^c   Miyata, Mikiji ^c   Naito, Takeaki ^a  

^a KOBE PHARMACEUTICAL UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

^c OSAKA UNIVERSITY   (Japan)

Author keywords

3,3 Sigmatropic rearrangement; Dienylimine; Indole; Indoline; N Trifluoroacetyl enehydrazines

Indexed keywords

BENZENE DERIVATIVE; CYCLOPENTENE DERIVATIVE; HYDRAZINE DERIVATIVE; INDOLE DERIVATIVE; SOLVENT;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; CYCLIZATION; PRIORITY JOURNAL; QUANTUM YIELD; REACTION ANALYSIS; SYNTHESIS;

EID: 33645011706     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.01.087     Document Type: Article

References (52)

1. Reviews of indole synthesis: (a) G.W. Gribble Contemp. Org. Synth. 1994 145
2. C.J. Moody Synlett 1994 681
3. T.L. Gilchrist J. Chem. Soc., Perkin Trans. 1 1999 2848
4. G.W. Gribble J. Chem. Soc., Perkin Trans. 1 2000 1045
5. Reviews of Fischer indole synthesis: (a) B. Robinson Chem. Rev. 63 1963 373
6. B. Robinson Chem. Rev. 69 1969 227
7. B. Robinson The Fischer Indole Synthesis 1982 Wiley New York
8. D.L. Hughes Org. Prep. Proced. Int. 25 1993 609
9. A.H. Kelly, D.H. McLeod, and J. Parrick J. Chem. Soc. 1965 296
10. M.M. Kidwai, and V.K. AhLuwalia Indian J. Chem. 27B 1988 962
11. F.M. Miller, and W.N. Schinske J. Org. Chem. 43 1978 3384
12. D.L. Hughes, and D. Zhao J. Org. Chem. 58 1993 228
13. D. Zhao, D.L. Hughes, D.R. Bender, A.M. DeMarco, and P.J. Reider J. Org. Chem. 56 1991 3001
14. K. Maruoka, M. Oishi, and H. Yamamoto J. Org. Chem. 58 1993 7638
15. Although the Fischer indolization of N-acetyl enehydrazine has previously been reported, it required either an elevated temperature (170°C) or an acid catalysis (dichloroacetic acid) to achieve successful cyclization. P. Schiess, and E. Sendi Helv. Chim. Acta 61 1978 1364
16. O. Miyata, Y. Kimura, K. Muroya, H. Hiramatsu, and T. Naito Tetrahedron Lett. 40 1999 3601
17. O. Miyata, Y. Kimura, and T. Naito Chem. Commun. 1999 2429
18. O. Miyata, Y. Kimura, and T. Naito Synthesis 2001 1635
19. O. Miyata, N. Takeda, and T. Naito Heterocycles 57 2002 1101
20. J. Goerdeler, and M. Bischoff Chem. Ber. 105 1972 3566
21. M. Okimoto, Y. Takahashi, and T. Kakuchi Synthesis 2003 2057
22. C. Liljebris, J. Martinsson, L. Tedenborg, M. Williams, E. Barker, J.E.S. Duffy, A. Nygren, and S. James Bioorg. Med. Chem. 10 2002 3197
23. D.C. Duncan, T.A. Trumbo, C.D. Almquist, T.A. Lentz, and C.F. Beam J. Heterocycl. Chem. 24 1987 555
24. Odera, T.; Sato, M. Patent JP 2000169446, 2000; Chem. Abstr. 2000, 133, 17376.
25. S.D. Sharma, and S.B. Pandhi J. Org. Chem. 55 1990 2196
26. R.J. Moran, C. Cramer, and D.E. Falvey J. Org. Chem. 62 1997 2742
27. Torizuka, K. Patent JP 2001175012; Chem. Abstr. 2001, 135, 68523.
28. P.L. Southwick, B. McGrew, R.R. Engel, G.E. Milliman, and R.J. Owellen J. Org. Chem. 28 1963 3058
29. M.K. Eberle, and L. Brzechffa J. Org. Chem. 41 1976 3775
30. K. Bast, T. Durst, R. Huisgen, K. Lindner, and R. Temme Tetrahedron 54 1998 3745
31. J.G. Rodriguez, and A. San Andres J. Heterocycl. Chem. 28 1991 1293
32. T. Iwama, V.B. Birman, S.A. Kozmin, and V.H. Rawal Org. Lett. 1 1999 673
33. J.E. Ney, and J.P. Wolfe J. Am. Chem. Soc. 127 2005 8644
34. S.D. Sharma, and S.B. Pandhi J. Org. Chem. 55 1990 2196
35. J.C. Antilla, A. Klapars, and S.L. Suchwald J. Am. Chem. Soc. 124 2002 11684
36. G.-S. Zhang, and B. Chai Synth. Commun. 30 2000 1849
37. R.P. Linstead J. Chem. Soc. 1929 2493
38. N. Moskalev, M. Barbasiewicz, and M. Makosza Tetrahedron 60 2004 347
39. C. Caubere, P. Caubere, S. Ianelli, M. Nardelli, and B. Jamart-Gregoire Tetrahedron 50 1994 11903
40. A.P. Dobbs, M. Voyle, and N. Whittall Synlett 1999 1594
41. 10b
42. N. Lachance, and W.Y. Chan J. Heterocycl. Chem. 40 2003 289
43. B. Robinson J. Heterocycl. Chem. 24 1987 1321
44. H. Ishii Acc. Chem. Res. 14 1981 275
45. Y. Murakami, H. Yokoo, Y. Yokoyama, and T. Watanabe Chem. Pharm. Bull. 47 1999 791
46. G.S. Bajwa, and R.K. Brown Can. J. Chem. 47 1969 785
47. G.S. Bajwa, and R.K. Brown Can. J. Chem. 48 1970 2293
48. B.-C. Chen, J. Hynes Jr., C.R. Pandit, R. Zhao, A.P. Skoumbourdis, H. Wu, J.E. Sundeen, and K. Leftheris Heterocycles 55 2001 951
49. P.P. Garner, D.T. Parker, J.J. Gajewski, A. Lubineau, J. Ange, Y. Queneau, I.P. Beletskaya, A. Cheprakov, F. Fringuelli, O. Piermatti, F. Pizzo, and S. Kobayashi P.A. Grieco Organic Synthesis in Water 1998 Blackie Academic and Professional London
50. J.P. Massey, and S.G.P. Plant J. Chem. Soc. 1931 1990
51. N. Lachance, and W.Y. Chan J. Heterocycl. Chem. 40 2003 289
52. Bently, J. M.; Roffey, J. R. A.; Davidson, J. E. P.; Mansell, H. L.; Hamlyn, R. J.; Cliffe, I. A.; Adams, D. R.; Monck, N. J. Patent WO 2001012603, 2001; Chem. Abstr. 2001, 134, 193339.