3-lithio-1-(triisopropylsilyl)indole, preparation and reactions with electrophilic reagents

Heterocycles

Volumn 43, Issue 8, 1996, Pages 1713-1718

  Amat, Mercedes ^a   Sathyanarayana, Swargam ^a   Hadida, Sabine ^a   Bosch, Joan ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000218630     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-96-7504     Document Type: Article

References (19)

1. R. J. Sundberg, "The Chemistry of Indoles", Academic Press, New York, 1970, Chapter 1; R. A. Jones, "Comprehensive Heterocyclic Chemistry", Vol. 4, ed, by A. R. Katritzky and C. W. Rees, Pergamon Press, Oxford, 1984, pp. 201-312; R. J. Sundberg, "Progress in Heterocyclic Chemistry", Vol. 7, ed. by H. Suschitzky and E. F. V. Scriven, Pergamon, Oxford, 1995, Chapter 5, part 2, and previous volumes in this series.
2. R. J. Sundberg, "The Chemistry of Indoles", Academic Press, New York, 1970, Chapter 1; R. A. Jones, "Comprehensive Heterocyclic Chemistry", Vol. 4, ed, by A. R. Katritzky and C. W. Rees, Pergamon Press, Oxford, 1984, pp. 201-312; R. J. Sundberg, "Progress in Heterocyclic Chemistry", Vol. 7, ed. by H. Suschitzky and E. F. V. Scriven, Pergamon, Oxford, 1995, Chapter 5, part 2, and previous volumes in this series.
3. R. J. Sundberg, "The Chemistry of Indoles", Academic Press, New York, 1970, Chapter 1; R. A. Jones, "Comprehensive Heterocyclic Chemistry", Vol. 4, ed, by A. R. Katritzky and C. W. Rees, Pergamon Press, Oxford, 1984, pp. 201-312; R. J. Sundberg, "Progress in Heterocyclic Chemistry", Vol. 7, ed. by H. Suschitzky and E. F. V. Scriven, Pergamon, Oxford, 1995, Chapter 5, part 2, and previous volumes in this series.
4. For recent references, see: M. Somei and T. Kobayashi, Heterocycles, 1992, 34, 1295; W.G. Gribble, D. J. Keavy, D. A. Davis, M. G. Saulnier, B. Pelcman, T. C. Barden, M. P. Sibi, E. R. Olson, and J. J. BelBruno, J. Org. Chem., 1992, 57, 5878 ; T. Sakamoto, Y. Kondo, N. Takazawa, and H. Yamanaka, Heterocycles, 1993, 36, 941; M. Amat, S. Hadida, and J. Bosch, Tetrahedron Lett., 1994, 35, 793; S. S. Labadie and E. Teng, J. Org. Chem., 1994, 59, 4250. See also references cited therein.
5. For recent references, see: M. Somei and T. Kobayashi, Heterocycles, 1992, 34, 1295; W.G. Gribble, D. J. Keavy, D. A. Davis, M. G. Saulnier, B. Pelcman, T. C. Barden, M. P. Sibi, E. R. Olson, and J. J. BelBruno, J. Org. Chem., 1992, 57, 5878 ; T. Sakamoto, Y. Kondo, N. Takazawa, and H. Yamanaka, Heterocycles, 1993, 36, 941; M. Amat, S. Hadida, and J. Bosch, Tetrahedron Lett., 1994, 35, 793; S. S. Labadie and E. Teng, J. Org. Chem., 1994, 59, 4250. See also references cited therein.
6. For recent references, see: M. Somei and T. Kobayashi, Heterocycles, 1992, 34, 1295; W.G. Gribble, D. J. Keavy, D. A. Davis, M. G. Saulnier, B. Pelcman, T. C. Barden, M. P. Sibi, E. R. Olson, and J. J. BelBruno, J. Org. Chem., 1992, 57, 5878 ; T. Sakamoto, Y. Kondo, N. Takazawa, and H. Yamanaka, Heterocycles, 1993, 36, 941; M. Amat, S. Hadida, and J. Bosch, Tetrahedron Lett., 1994, 35, 793; S. S. Labadie and E. Teng, J. Org. Chem., 1994, 59, 4250. See also references cited therein.
7. For recent references, see: M. Somei and T. Kobayashi, Heterocycles, 1992, 34, 1295; W.G. Gribble, D. J. Keavy, D. A. Davis, M. G. Saulnier, B. Pelcman, T. C. Barden, M. P. Sibi, E. R. Olson, and J. J. BelBruno, J. Org. Chem., 1992, 57, 5878 ; T. Sakamoto, Y. Kondo, N. Takazawa, and H. Yamanaka, Heterocycles, 1993, 36, 941; M. Amat, S. Hadida, and J. Bosch, Tetrahedron Lett., 1994, 35, 793; S. S. Labadie and E. Teng, J. Org. Chem., 1994, 59, 4250. See also references cited therein.
8. For recent references, see: M. Somei and T. Kobayashi, Heterocycles, 1992, 34, 1295; W.G. Gribble, D. J. Keavy, D. A. Davis, M. G. Saulnier, B. Pelcman, T. C. Barden, M. P. Sibi, E. R. Olson, and J. J. BelBruno, J. Org. Chem., 1992, 57, 5878 ; T. Sakamoto, Y. Kondo, N. Takazawa, and H. Yamanaka, Heterocycles, 1993, 36, 941; M. Amat, S. Hadida, and J. Bosch, Tetrahedron Lett., 1994, 35, 793; S. S. Labadie and E. Teng, J. Org. Chem., 1994, 59, 4250. See also references cited therein.
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11. Very recently, the preparation of 1-(benzenesulfonyl)-3-indolylmagnesium bromide and its reaction with electropilues to give 3-substituted indoles has been reported: Y. Kondo, A. Yoshida, S. Sato, and T. Sakamoto, Heterocycles, 1996, 42, 105.
12. M. G. Saulnier and G. W. Gribble, J. Org. Chem., 1982, 47, 757.
13. G. W. Gribble and M. G. Saulnier, J. Org. Chem., 1983, 48, 607.
14. M. Amat, S. Hadida, S. Sathyanarayana, and J. Bosch, J. Org. Chem., 1994, 59, 10.
15. C. Rücker, Chem. Rev., 1995, 95, 1009.
16. B. L. Bray, P. H. Mathies, R. Naef, D. R. Solas, T. T. Tidwell, D. R. Artis, and J. M. Muchowski, J. Org. Chem., 1990, 55, 6317, and references cited therein.
17. P. J. Beswick, C. S. Greenwood, T. J. Mowlem, G. Nechvatal, and D. A. Widdowson, Tetrahedron, 1988, 44, 7325; M. Iwao, Heterocycles, 1993, 36, 29,
18. P. J. Beswick, C. S. Greenwood, T. J. Mowlem, G. Nechvatal, and D. A. Widdowson, Tetrahedron, 1988, 44, 7325; M. Iwao, Heterocycles, 1993, 36, 29,
19. 13C-nmr) and elemental analysis or by comparison with authentic samples.