Nucleophilic substitution reaction at the 1-position of 1-hydroxytryptamine and -tryptophan derivatives

Heterocycles

Volumn 61, Issue , 2003, Pages 163-172

  Yamada, Fumio ^a   Goto, Aya ^a   Peng, Wu ^a   Hayashi, Toshikatsu ^a   Saga, Yoshitomo ^a   Somei, Masanori ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 HYDROXYTRYPTAMINE DERIVATIVE; TRYPTAMINE DERIVATIVE; TRYPTOPHAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; X RAY CRYSTALLOGRAPHY;

EID: 0347652965     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (27)

1. a) Dedicated to the 30th Anniversary of Heterocycles.
2. This is Part 120 of a series entitled "The Chemistry of Indoles".
3. Part 119: Y. Nakai, A. Goto, F. Yamada, and M. Somei, Heterocycles, 2003, 60, 1589.
4. R. J. Sundberg, The Chemistry of Indoles, Academic Press, 1970; R. T. Brown, J. A. Joule, and P. G. Sammes, Comprehensive Organic Chemistry, Vol. 4, Pergamon Press, 1979, pp. 411-492; R. J. Sundberg, Indoles, Academic Press, 1996.
5. R. J. Sundberg, The Chemistry of Indoles, Academic Press, 1970; R. T. Brown, J. A. Joule, and P. G. Sammes, Comprehensive Organic Chemistry, Vol. 4, Pergamon Press, 1979, pp. 411-492; R. J. Sundberg, Indoles, Academic Press, 1996.
6. R. J. Sundberg, The Chemistry of Indoles, Academic Press, 1970; R. T. Brown, J. A. Joule, and P. G. Sammes, Comprehensive Organic Chemistry, Vol. 4, Pergamon Press, 1979, pp. 411-492; R. J. Sundberg, Indoles, Academic Press, 1996.
7. a) "1-Hydroxyindole Hypotheses" was first presented orally: M. Somei, Y. Karasawa, S. Tokutake, T. Shoda, F. Yamada, and C. Kaneko, Abstracts of Papers, The 13th Congress of Heterocyclic Chemistry, Shizuoka, Nov. 1980, p. 33;
8. b) M. Somei, J. Synth. Org. Chem., 1991, 49, 205;
9. c) M. Somei, T. Kawasaki, Y. Fukui, F. Yamada, T. Kobayashi, H. Aoyama, and D. Shinmyo, Heterocycles, 1992, 34, 1877.
10. Review: M. Somei, Heterocycles, 1999, 50, 1157; M. Somei, Advances in Heterocyclic Chemistry, Vol. 82, ed. by A. R. Katritzky, Elsevier Science, USA, 2002, pp. 101-155.
11. Review: M. Somei, Heterocycles, 1999, 50, 1157; M. Somei, Advances in Heterocyclic Chemistry, Vol. 82, ed. by A. R. Katritzky, Elsevier Science, USA, 2002, pp. 101-155.
12. M. Somei, F. Yamada, T. Hayashi, A. Goto, and Y. Saga, Heterocycles, 2001, 55, 457; T. Hayashi, W. Peng, Y. Nakai, K. Yamada, and M. Somei, ibid., 2002, 57, 421.
13. M. Somei, F. Yamada, T. Hayashi, A. Goto, and Y. Saga, Heterocycles, 2001, 55, 457; T. Hayashi, W. Peng, Y. Nakai, K. Yamada, and M. Somei, ibid., 2002, 57, 421.
14. P. Seidel, Ber., 1944, 77, 796.
15. B. Oddo, Gazz. Chim. Ital., 1913, 43, 385; K. Keller, Ber., 1913, 46, 726; G. F. Smith, Chem. and Ind. (London), 1954, 1451; G. F. Smith, Advan. Heterocyclic Chem., 1963, 2, 300; W. E. Noland and W. C. Kuryla, J. Org. Chem., 1960, 25, 486.
16. B. Oddo, Gazz. Chim. Ital., 1913, 43, 385; K. Keller, Ber., 1913, 46, 726; G. F. Smith, Chem. and Ind. (London), 1954, 1451; G. F. Smith, Advan. Heterocyclic Chem., 1963, 2, 300; W. E. Noland and W. C. Kuryla, J. Org. Chem., 1960, 25, 486.
17. B. Oddo, Gazz. Chim. Ital., 1913, 43, 385; K. Keller, Ber., 1913, 46, 726; G. F. Smith, Chem. and Ind. (London), 1954, 1451; G. F. Smith, Advan. Heterocyclic Chem., 1963, 2, 300; W. E. Noland and W. C. Kuryla, J. Org. Chem., 1960, 25, 486.
18. B. Oddo, Gazz. Chim. Ital., 1913, 43, 385; K. Keller, Ber., 1913, 46, 726; G. F. Smith, Chem. and Ind. (London), 1954, 1451; G. F. Smith, Advan. Heterocyclic Chem., 1963, 2, 300; W. E. Noland and W. C. Kuryla, J. Org. Chem., 1960, 25, 486.
19. B. Oddo, Gazz. Chim. Ital., 1913, 43, 385; K. Keller, Ber., 1913, 46, 726; G. F. Smith, Chem. and Ind. (London), 1954, 1451; G. F. Smith, Advan. Heterocyclic Chem., 1963, 2, 300; W. E. Noland and W. C. Kuryla, J. Org. Chem., 1960, 25, 486.
20. M. Somei, T. Kawasaki, Y. Fukui, F. Yamada, T. Kobayashi, H. Aoyama, and D. Shinmyo, Heterocycles, 1992, 34, 1877; M. Somei, N. Oshikiri, M. Hasegawa, and F. Yamada, ibid., 1999, 51, 1237; M. Hasegawa, Y. Nagahama, K. Kobayashi, M. Hayashi, and M. Somei, ibid., 2000, 52, 483; Y. Fukui and M. Somei, ibid., 2001, 55, 2055.
21. M. Somei, T. Kawasaki, Y. Fukui, F. Yamada, T. Kobayashi, H. Aoyama, and D. Shinmyo, Heterocycles, 1992, 34, 1877; M. Somei, N. Oshikiri, M. Hasegawa, and F. Yamada, ibid., 1999, 51, 1237; M. Hasegawa, Y. Nagahama, K. Kobayashi, M. Hayashi, and M. Somei, ibid., 2000, 52, 483; Y. Fukui and M. Somei, ibid., 2001, 55, 2055.
22. M. Somei, T. Kawasaki, Y. Fukui, F. Yamada, T. Kobayashi, H. Aoyama, and D. Shinmyo, Heterocycles, 1992, 34, 1877; M. Somei, N. Oshikiri, M. Hasegawa, and F. Yamada, ibid., 1999, 51, 1237; M. Hasegawa, Y. Nagahama, K. Kobayashi, M. Hayashi, and M. Somei, ibid., 2000, 52, 483; Y. Fukui and M. Somei, ibid., 2001, 55, 2055.
23. M. Somei, T. Kawasaki, Y. Fukui, F. Yamada, T. Kobayashi, H. Aoyama, and D. Shinmyo, Heterocycles, 1992, 34, 1877; M. Somei, N. Oshikiri, M. Hasegawa, and F. Yamada, ibid., 1999, 51, 1237; M. Hasegawa, Y. Nagahama, K. Kobayashi, M. Hayashi, and M. Somei, ibid., 2000, 52, 483; Y. Fukui and M. Somei, ibid., 2001, 55, 2055.
24. Acheson and co-workers have reported that 1-benzoyloxyindole has also a pyramidal nitrogen atom (N-1); R. M. Acheson, M. H. Benn, J. Jacyno, and J. D. Wallis, J. Chem. Soc., Perkin Trans. 2, 1983, 497.
25. Substitution reactions on the nitrogen of hydroxylamines are reviewed: K. Shudo, J. Synth. Org. Chem., 1973, 31, 395; T. Ohta, K. Shudo, and T. Okamoto, Tetrahedron Lett., 1978, 1983 and references cited therein.
26. Substitution reactions on the nitrogen of hydroxylamines are reviewed: K. Shudo, J. Synth. Org. Chem., 1973, 31, 395; T. Ohta, K. Shudo, and T. Okamoto, Tetrahedron Lett., 1978, 1983 and references cited therein.
27. C. J. Gilmore, J. Appl. Cryst., 1984, 17, 42.