Palladium(II)-mediated oxidative cyclization of N-carbamoyl aminoalkynes: A new route to γ-lactams

Tetrahedron Letters

Volumn 40, Issue 37, 1999, Pages 6765-6768

  Doan, Huynh Dong ^a   Goré, Jacques ^a   Vatèle, Jean Michel ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

Lactams; Alkynes; Carbamates; Cyclization; Palladium catalysts

Indexed keywords

2 PYRROLIDONE DERIVATIVE; ALKYNE DERIVATIVE; AMINE; CARBAMIC ACID DERIVATIVE; GAMMA LACTAM DERIVATIVE; PALLADIUM;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CYCLIZATION; DRUG SYNTHESIS; STRUCTURE ANALYSIS;

EID: 0033543533     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01305-2     Document Type: Article

References (48)

1. (a) Tchissambou, L.; Benechie, M.; Khuong-Huu, F. Tetrahedron 1982, 38, 2687-2695;
2. (b) Papke, U.; Gross, E. M.; Francke, W. Tetrahedron Lett. 1997, 38, 379-382.
3. (a) Meyers, A. I.; Snyder, L. J. Org. Chem. 1993, 58, 36-42;
4. (b) Rigo, B.; Fasseur, D.; Cherepy, N.; Couturier, D. Tetrahedron Lett. 1989, 30, 7057-7060.
5. Nilsson, B. M.; Ringdahl, B.; Hacksell, U. J. Med. Chem. 1990, 33, 580-584.
6. Bergmann, R.; Gericke, R. J. Med. Chem. 1990, 33, 492-504.
7. (a) Garvey, D. S.; May, P. D.; Nadzan, A. M. J. Org. Chem. 1990, 55, 936-940;
8. (b) Eda, N. J.; Rae, I. D.; Hearn, M. T. W. Aust. J. Chem. 1991, 44, 891-894.
9. Smith, M. B.; Dembofsky, B. T.; Chan Son, Y. J. Org. Chem. 1994, 59, 1719-1725.
10. (a) Winkler, J. D.; Hershberger, P. M. J. Am. Chem. Soc. 1989, 111, 4852-4856;
11. (b) Hamada, Y.; Hara, O.; Kawai, A.; Kohno, Y.; Shioiri, T. Tetrahedron 1991, 40, 8635-8652;
12. (c) Yoda, H.; Kitayama, H.; Katagiri, T.; Takabe, K. Tetrahedron 1992, 48, 3313-3322;
13. (d) Bänziger, M.; McGarrity, J. F.; Meul, T. J. Org. Chem. 1993, 58, 4010-4012;
14. (f) Nebois, P.; Greene, A. E. J. Org. Chem. 1996, 61, 5210-5211;
15. (g) Kanazawa, A.; Gillet, S.; Delair, P.; Greene, A. E. J. Org. Chem. 1998, 63, 4660-4663;
16. (h) Snider, B. B.; Lin, H.; Foxman, B. M. J. Org. Chem. 1998, 63, 6442-6443;
17. (i) Snider, B. B.; Ahn, Y.; Foxman, B. M. Tetrahedron 1999, 40, 3339-3342.
18. (a) Burgess, L. E.; Meyers, A. I. J. Org. Chem. 1992, 57, 1656-1662, and references cited therein;
19. (b) Ikeda, M.; Sato, T.; Ishibashi, H. Heterocycles 1988, 27, 1465-1487;
20. (c) Liddell, J. R. Nat. Prod. Rep. 1996, 13, 187-193.
21. (a) Burgess, L. E.; Meyers, A. I. J. Am. Chem. Soc. 1991, 113, 9858-9859;
22. (b) Wei, Z. Y.; Knaus, E. E. Synlett 1993, 295-296;
23. (c) McAlonan, H.; Stevenson, P. J. Tetrahedron: Asymmetry 1995, 6, 239-244.
24. For a review, see: Ogliaruso, M. A.; Wolfe, J. F. Synthesis of Lactones and Lactames; Patai, S.; Rappoport, Z., Eds.; John Wiley: New York, 1993; pp. 132-252 and 397-957.
25. For more recent methods of γ-lactam synthesis, see, for example: (a) Ha, D. C.; Kang, S.; Chung, C. M.; Lim, H. K. Tetrahedron Lett. 1998, 39, 7541-7544;
26. (b) Machrouhi, F.; Namy, J. L. Tetrahedron 1998, 54, 11111-11122;
27. (c) Rigby, J. H.; Danca, D. M.; Horner, J. H. Tetrahedron Lett. 1998, 39, 8413-8416;
28. (d) Ryu, I.; Matsu, K.; Minakata, S.; Komatsu, M. J. Am. Chem. Soc. 1998, 120, 5838-5839.
29. (a) Compain, P.; Vatèle, J. M.; Goré, J. Synlett 1994, 943-945;
30. (b) Compain, P.; Goré, J.; Vatèle, J. M. Tetrahedron 1996, 52, 10405-10416.
31. These amines were prepared using known procedures: (a) from the corresponding alcohol for 1a-e and 11-n;
32. (b) from 2-iodoaniline for 1j,k, see: Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1989, 30, 2581-2584;
33. (c) from the corresponding homopropargylic acid using a Curtius rearrangement for 1f-i, see: Miller, R. D.; Goelitz, P. J. Org. Chem. 1981, 46, 1616-1618.
34. McDonald, F. E.; Chatterjee, A. K. Tetrahedron Lett. 1997, 38, 7687-7690.
35. (a) Nagasaka, T.; Sato, H.; Saeki, S. Tetrahedron: Asymmetry 1997, 8, 191-194;
36. (b) Braun, N. A.; Ciufolini, M. A.; Peters, K.; Peters, E. M. Tetrahedron Lett. 1998, 39, 4667-4670.
37. (a) Hill, R. K. J. Org. Chem. 1957, 22, 830-832;
38. (b) Bailey, P. D.; Morgan, K. M.; Smith, D. I.; Vernon, J. M. Tetrahedron Lett. 1994, 35, 7115-7118.
39. Indeed, compounds 1j,k are known to be poor substrates in the transition metal-catalyzed synthesis of indoles, see: (a) Iratani, K.; Matsubara, S.; Utimoto, K. Tetrahedron Lett. 1988, 29, 1799-1802;
40. (b) Xu, L.; Lewis, I. R.; Davidsen, S. K.; Summers, J. B. Tetrahedron Lett. 1998, 39, 5159-5162.
41. Fukada, Y.; Shiragami, H.; Utimoto, K.; Nozaki, H. J. Org. Chem. 1991, 56, 5816-5819.
42. (a) White, J. D.; Sommers, J. C.; Nagabushana Reddy, G. J. Org. Chem. 1992, 57, 4991-4998;
43. (b) Kano, S.; Yuasa, Y.; Asami, K.; Shibuya, S. Chem. Lett. 1986, 735-736.
44. Wei, Z. Y.; Knaus, E. E. Tetrahedron Lett. 1994, 35, 847-848.
45. 20 +16 (c 1, EtOH)].
46. (a) Andruszkiewicz, R.; Silverman, R. B. J. Biol. Chem. 1990, 265, 22288-22291;
47. (b) Otsuka, M.; Masuda, T.; Haupt, A.; Ohno, M.; Shiraki, T.; Sugiura, Y.; Maeda, K. J. Am. Chem. Soc. 1990, 112, 838-845;
48. (c) Artis, D. R.; Cho, I. S.; Jaime-Figueroa, S.; Muchowski, J. M. J. Org. Chem. 1994, 59, 2456-2466.