Intramolecular cyclization of β-alkynylpropanamides to γ-alkylidene-γ-butyrolactams

Tetrahedron Letters

Volumn 39, Issue 21, 1998, Pages 3517-3520

  Koseki, Yuji ^a   Kusano, Shuichi ^a   Nagasaka, Tatsuo ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

GAMMA BUTYROLACTONE DERIVATIVE; PROPIONAMIDE DERIVATIVE;

ARTICLE; CYCLIZATION; REACTION ANALYSIS;

EID: 0032554962     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00520-6     Document Type: Article

References (31)

1. a) March, J. Advanced Organic Chemistry, 4th ed.; J. Wiley & Sons: New York, 1992; pp 768-770.
2. b) Utimoto, K. Yuki Gousei Kagaku Kyokaishi 1987, 45, 112-122.
3. a) Utimoto, K. Pure Appl Chem. 1983, 55, 1845-1852.
4. b) Tokuda, M.; Fujita, H.; Nitta, M.; Suginome, H. Heterocycles 1996, 42, 385-395.
5. c) Tokuda, M.; Fujita, H.; Suginome, H. Tetrahedron Lett. 1990, 31, 5353-5356.
6. a) For the hydroamination of alkynylamine, see: Li, Y.; Marks, T.J. J. Am. Chem. Soc. 1996, 118, 9295-9306, and references therein.
7. b) Luo, F-T.; Wang, R-T. Tetrahedron Lett. 1992, 33, 6835-6838.
8. c) Tamara, Y.; Kimura, M. Synlett 1997, 749-757.
9. d) Fukuda, Y.; Matsubara, S.; Utimoto, K. J. Org. Chem. 1991, 56, 5812-5816.
10. e) Fukuda, Y.; Utimoto, K.; Nozaki, H. Heterocycles 1987, 25, 297-300.
11. a) Wensbo, D.; Eriksson, A.; Jeschke, T.; Annby, U.; Gronowitz, S. Tetrahedron Lett. 1993, 34, 2823-2826.
12. b) Arcadi, A.; Cacchi, S.; Carnicelli, V.; Marinelli, F. Tetrahedron 1994, 50, 437-452.
13. c) Larock, R.C.; Yum, E.K., J. Am. Chem. Soc. 1991, 113, 6689-6690.
14. d) Sakamoto, T.; Kondo, Y.; Iwashita, S.; Nagano, T.; Yamanaka, H. Chem. Pharm. Bull. 1988, 36, 1305-1308.
15. a) Jacobi, P.A.; Brielmann, H.L.; Hauck, S.I. J. Org. Chem. 1996, 61, 5013-5023.
16. b) Jacobi, P.A.; Rajeswari, S. Tetrahedron Lett. 1992, 33, 6235-6238.
17. Yoshimatsu, M.; Machida, K.; Fuseya, T.; Shimizu, H.; Kataoka, T. J. Chem. Soc., Perkin Trans. 1 1996, 1839-1843.
18. a) Bouyssi, D.; Cavicchioli, M.; Balme, G. Synlett 1997, 944-946.
19. b) Arcadi, A. Synlett 1997, 941-943.
20. c) Kimura, M.; Wakamiya Y.; Horino, Y.; Tamaru, Y. Tetrahedron Lett. 1997, 38, 3963-3966.
21. d) Tamaru, Y.; Kimura, M.; Tanaka, S; Kure, S.; Yoshida, Z. Bull. Chem. Soc. Jpn. 1994, 67, 2838-2849.
22. e) Reference 3c,
23. f) Ohe, K.; Ishihara, T.; Chatani, N.; Kawasaki, Y.; Murai, S. J. Org. Chem. 1991, 56, 2267-2268.
24. g) Shachat, N.; Bagnell, J.J., Jr. J. Org. Chem. 1963, 28, 991-995.
25. Koseki, Y.; Nagasaka, T. Chem. Pharm. Bull. 1995, 43, 1604-1606.
26. 1 = Me) from I by a little different conditions was reported in a total yield of 35% ; Carling, R.W.; Clark, J.S.; Holmes, A.B.; Sartor, D. J. Chem. Soc., Perkin Trans 1 1992, 95-101.
27. 2: C, 73.44; H, 7.81; N, 5.71. Found: C, 73.42; H, 7.81; N, 5.68.
28. 7d, 7f).
29. 2 / AgOTf (2:1) in toluene was added via syringe at r.t. to a solution of 1i in toluene to form a black-brown precipitate gradually, followed by the same work-up described for general procedure to afford 2i in 86% yield.
30. 3).
31. 3 at r.t. for several hours. (Chemical Equation Presented) Tetrahedron Letters 39 (1998) 3521-3524