Regioselective cyclization of 1-trimethylacetylindole derivatives at the 4-position of indole nucleus

Heterocyclic Communications

Volumn 3, Issue 1, 1997, Pages 47-50

  Nakatsuka, Shin Ichi ^a   Hayashi, Takuji ^a   Adachi, Shogo ^a   Harada, Yasunari ^a   Tajima, Nobumitsu ^a  

^a GIFU UNIVERSITY   (Japan)

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EID: 0142053676     PISSN: 07930283     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (16)

1. H. G. Floss, Tetrahedron, 32, 873(1976).
2. J. Szmuszkovicz, J. Org. Chem., 29, 843(1964) and references cited in (3cd).
3. a) S. Nakatsuka, H. Miyazaki and T. Goto, Tetrahedron Lett., 21, 2817(1980)
4. b) S. Nakatsuka, H. Miyazaki and T. Goto, Chem. Lett., 407(1981)
5. c) S. Nakatsuka, K. Yamada and T.Goto, Tetrahedron Lett., 27, 4757(1986)
6. d) K. Teranishi, S. Hayashi, S. Nakatsuka and T. Goto, ibid., 35, 8173(1994) and Synthesis, 506(1995).
7. d) K. Teranishi, S. Hayashi, S. Nakatsuka and T. Goto, ibid., 35, 8173(1994) and Synthesis, 506(1995).
8. J. B. Brown, H. B. Henbest and E. R. H. Jones, J. Chem. Soc., 3172(1952).
9. 3) δ 1.27(3H, d, J=7Hz), 1.51(9H, s), 1.87(2H. q, J=8Hz), 2.81(2H,m), 3.92(1H, m), 7.24∼7.37(3H, m), 7.52(1H, d, J=8Hz), 8.51(1H,d, J=8Hz).
10. J. Szmuszkovicz, J. Am. Chem. Soc., 79, 2819(1957).
11. 3) δ 1.38(3H, d, J=7Hz), 1.51(9H. s), 1.76(1H, m), 2.08(1H, m), 2.82(2H, m), 3.07(1H, m), 7.10(1H, br.d, J=8Hz), 7.29(1H, t, J=8Hz), 7.36(1H, br.s), 8.18(1H, br.d, J=8Hz).
12. 3) δ 1.34(6H, s), 1.51(9H, s), 1.84(2H, t, J=6Hz), 2.84(2H, t, J=6Hz), 7.17(1H, br.d, J=8Hz), 7.30(1H, t, J=8Hz), 7.38(1H, br.s), 8.18(1H, br.d, J=8Hz).
13. 3) δ 1.51(9H, s), 1.71(3H, m), 3.39(2H, m), 5.66(2H, m), 7.21-7.39(2H, m), 7.47(1H, br.s), 7.52(1H, br.d, J=8Hz), 8.51(1H, br.d, J=8Hz).
14. 3) δ 1.45(9H, s), 1.78(6H, m), 3.39(2H, d, J=7Hz), 5.40(1H, m), 7.22-7.38(2H, m), 7.43(1H, br.s), 7.50(1H, br.d, J=8Hz), 8.50(1H, br.d, J=8Hz).
15. 3) δ 1.40(3H, d, J=7Hz), 1.78(1H, m), 2.10(1H, m), 2.88(2H, m), 3.10(1H, m), 6.85(1H, m), 6.92(1H, m), 7.14-7.17(2H, m), 7.83(1H, br.s).
16. 3) δ 1.35 (6H, s), 1.86(2H, t, J=7Hz), 2.89(2H, t, J=7Hz), 6.86(1H, m), 6.99(1H, br. t, J=8Hz), 7.16(2H, m), 7.84(1H, br.s).