Regio-controlled cyclization of 1-(3-methyl-2-butenoyl)indoles at their 2 and 7-positions

Heterocyclic Communications

Volumn 2, Issue 6, 1996, Pages 555-558

  Nakatsuka, Shin Ichi ^a   Hu, Dingyu ^a   Tanahashi, Mitsuhiko ^a  

^a GIFU UNIVERSITY   (Japan)

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[No Author keywords available]

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EID: 0043212480     PISSN: 07930283     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (24)

1. a) H. Nakata, H. Harada and Y. Hirata, Tetrahedron Lett., 2125(1966).
2. b) H. Harada, N. Sakabe, Y. Hirata, Y. Tomiie and I. Nitta, Bull. Chem. Soc. Japan, 39, 1773(1966).
3. a) G. Castani, R. Cavalleri, F. Piozzi and A. Quilico, Gazz. Chem. Ital., 92, 105(1962).
4. b) R. Romanet, A. Chemizart, S. Duhoux and S. David, Bull. Soc. Chim. France, 1048(1963).
5. R.J. Sundberg, The Chemistry of Indole, published by Academic press, 1970.
6. a) S. Nakatsuka, H. Miyazaki and T. Goto, Tetrahedron Lett., 21, 2817(1980).
7. b) S. Nakatsuka, H. Miyazaki and T. Goto, Chem. Lett., 407(1981).
8. c) S. Nakatsuka, K. Yamada and T. Goto, Tetrahedron Lett., 27, 4757(1986).
9. d) S. Nakatsuka, O. Asano, K. Ueda and T. Goto, Heterocycles, 26, 1471(1987).
10. e) S. Nakatsuka et al., Tetrahedron Lett., 35, 8173(1994) and Synthesis, 506 (1995).
11. e) S. Nakatsuka et al., Tetrahedron Lett., 35, 8173(1994) and Synthesis, 506 (1995).
12. a) S. Nakatsuka, T. Masuda, O. Asano, T. Teramae and T. Goto, Tetrahedron Lett., 27, 4327(1986)
13. b) S. Nakatsuka, T. Masuda, K. Sakai, and T. Goto, ibid., 27, 6245(1986)
14. c) T. Masuda, K. Ueda, O. Asano, S. Nakatsuka and T. Goto, Heterocycles, 26, 1475(1987).
15. d) S. Nakatsuka, T. Masuda, K. Sakai and T. Goto, Tetrahedron Lett., 27, 5735(1986).
16. e) S. Nakatsuka, T. Masuda and T. Goto, ibid., 28, 3671(1987).
17. 2, 4) 130°C, 8% overall yield].
18. These derivatives were obtained by N-acylation(NaH/RC0C1 in DMF) of methyl indole-3-carboxylate in quant. yields.
19. 3) δ 2.08(3H, br.s), 2.24 (3H, br.s), 3.96(3H, s), 6.42(1H, br.s), 7.39(2H, m), 8.15(1H, m), 8.23(1H, s), 8.45(1H, m).
20. 3) δ 1.45(6H, s), 2.88 (2H, s), 3.94(3H, s), 7.26(1H, br,d, J=8Hz), 7.35(1H, t, J=8Hz), 7.94(1H, br.d, J=8Hz), 8.31(1H, s).
21. 3) δ 2.03(3H, br.s), 2.18 (3H, br.s), 2.28(3H, br.s), 6.34(1H, br.s), 7.28(1H, br.s), 7.33(2H, m), 7.50(1H, br.d, J=8Hz), 8.43(1H, br.d, J=8Hz).
22. 3) δ 1.42(6H, s), 2.30 (3H, br.s), 2.80(2H, s), 7.18-7.29(2H, m), 7.38(1H, br.d, J=7Hz), 7.44(1H, br.s).
23. 3) δ 1.54(6H, s), 2.28 (3H, s), 2.92(2H, s), 7.29(2H, m), 7.43(1H, m), 8.02(1H, m).
24. 3) δ 1.53(6H, s), 2.33(3H, s), 5.10-5.16(2H, m), 6.10(1H, dd, J=16 & 10Hz), 7.09(2H, m), 7.29(1H, m), 7.49(1H, m), 7.82(1H, br.s).