An Efficient Synthetic Method of 4-Penteneselenoamides: Four-Component Coupling Reaction of Terminal Acetylenes, Selenium, Amines, and Allylic Bromides

Bulletin of the Chemical Society of Japan

Volumn 71, Issue 5, 1998, Pages 1193-1200

  Murai, Toshiaki ^a   Ezaka, Tatsuya ^a   Kato, Shinzi ^a  

^a GIFU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001054354     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.71.1193     Document Type: Article

References (22)

1. a) A. Ogawa and N. Sonoda, "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon, Oxford (1991). Vol. 6, p. 476;
2. b) A. Ogawa and N. Sonoda, Rev. Heteroatom Chem., 10, 43 (1994);
3. c) C. P. Dell, "Comprehensive Organic Functional Group Transformations," ed by A. R. Katritzky, O. Meth-Cohn, and C. W. Rees, Pergamon, Oxford (1995), Vol. 5, p. 624.
4. a) F. Malek-Yazdi and M. Yalpani, Synthesis, 1977, 328;
5. b) R. S. Sukhai, R. Jong, and L. Brandsma, Synthesis, 1977, 888;
6. c) R. S. Sukhai and L. Brandsma, Recl. Trav. Chim. Pays-Bas, 98, 55 (1979);
7. d) E. Schaumann and F.-F. Grabley, Tetrahedron Lett., 21, 4251 (1980);
8. e) P. A. Otten and A. van der Gen, Recl. Trav. Chim. Pays-Bas, 113, 499 (1994);
9. f) K Shimada, S. Akimoto, H. Itoh, H. Nakamura, and Y. Takikawa, Chem. Lett., 1994, 1743.
10. a) S. Kato, T. Komuro, T. Kanda, H. Ishihara, and T. Murai, J. Am. Chem. Soc., 115, 3000 (1993);
11. b) T. Murai, A. Hayashi, T. Kanda, and S. Kato, Chem. Lett., 1993, 1469;
12. c) T. Murai, H. Takada, T. Kanda, and S. Kato, Chem. Lett., 1995, 1057;
13. d) T. Murai, K. Kakami, N. Itoh, T. Kanda, and S. Kato, Tetrahedron, 52, 2839 (1996);
14. e) T. Murai, H. Takada, K. Kakami, M. Fujii, M. Maeda, and S. Kato, Tetrahedron, 53, 12237 (1997).
15. a) H. Ishihara, M. Yoshimi, N. Hara, H. Ando, and S. Kato, Bull. Chem. Soc. Jpn., 63, 835 (1990);
16. b) T. Murai, T. Ezaka, N. Niwa, T. Kanda, and S. Kato, Synlett, 1996, 865;
17. c) T. Murai, T. Ezaka, T. Kanda, and S. Kato, J. Chem. Soc., Chem. Commun., 1996, 1809;
18. d) T. Murai, T. Ezaka, T. Ichimiya, and S. Kato, Synlett, 1997, 775.
19. For example: a) I. Ugi, A. Dömling, and W. Hörl, Endeavour, 18, 115 (1994); b) T. A. Keating and R. W. Armstrong, J. Am. Chem. Soc., 118, 2574 (1996).
20. For example: a) I. Ugi, A. Dömling, and W. Hörl, Endeavour, 18, 115 (1994); b) T. A. Keating and R. W. Armstrong, J. Am. Chem. Soc., 118, 2574 (1996).
21. J. March, "Advanced Organic Chemistry," John Wiley & Sons, New York (1992), p. 248.
22. J. Suffert and D. Toussaint, J. Org. Chem., 60, 3550 (1995).