1,4-Reductive addition of hydrazoic acid to γ-oxo-α,β-unsaturated δ- lactones and -lactams: A convenient route to α-amino-γ-oxo-α,β- unsaturated δ-lactones and -lactams

European Journal of Organic Chemistry

Volumn , Issue 6, 1999, Pages 1449-1453

  Koulocheri, Sofia D ^a   Haroutounian, Serkos A ^a   Apostolopoulos, Costas D ^a   Chada, Raj K ^b   Couladouros, Elias A ^a,c  

^a AGRICULTURAL UNIVERSITY OF ATHENS   (Greece)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

^c INSTITUTE OF NANOSCIENCE AND NANOTECHNOLOGY   (Greece)

Author keywords

Hydrazoic acid; Oxo enamines; Reductive addition; Lactams; Lactones

Indexed keywords

HYDRAZONE DERIVATIVE; LACTAM DERIVATIVE; LACTONE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; REDUCTION; SYNTHESIS;

EID: 0032795214     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199906)1999:6<1449::AID-EJOC1449>3.0.CO;2-9     Document Type: Article

References (36)

1. [1a] M. T. Davies-Coleman, D. E. A. Rivett, Prog. Chem. Nat. Prod. 1989, 55, 1 -35.
2. [1b] C. W. Jefford, D. Jaggi, A. W. Sledeski, J. Boukouvalas in Studies in Natural Products Chemistry (Ed.: A. Rahman), Elsevier, Amsterdam, 1989, vol 3, pp. 157-171.
3. [2a] S. Kobayashi, R. Akiyama, M. Moriwaki, Tetrahedron Lett. 1997, 38, 4819-4822.
4. [2b] M. Tsuda, H. Shigemori, M. Ishibashi, T. Sasaki, J. Kobayashi, J. Org. Chem. 1992, 57, 3503-3507.
5. [2c] J. Lehman, B. Pieper, Tetrahedron: Asymmetry 1992, 3, 1537-1538.
6. [2d] W. Dai, J. A. Katzenellenbogen, J. Org. Chem. 1993, 58, 1900-1908.
7. [2e] C. Gravier-Pelletier, M. Saniere, I. Charvet, Y. Le Merrer, J.-C. Depezay, Tetrahedron Lett. 1994, 35, 115-118.
8. [2f] J. Lee. V. Marquez, N. E. Lewin, P. M. Blumberg, Synlett 1994, 206-208.
9. [2g] N. P. Baens, F. Compernolle, S. M. Toppet, G. J. Hoornaert, Tetrahedron 1993, 49, 3193-3202.
10. [3a] J. Bohrisch, H. Faltz, M. Patzel, J. Liebscher Tetrahedron 1994, 50, 10701-10708.
11. [3b] C. D. Apostolopoulos, M. P. Georgiadis, E. A. Couladouros, J. Heterocycl. Chem. 1996, 33, 7038-1744.
12. [4a] E. A. Couladouros, C. D. Apostolopoulos, Synlett 1996, 341-342.
13. [4b] E.A. Couladouros, C. D. Apostolopoulos, M. P. Georgiadis, Carbohydr. Res. 1993, 249, 399-404
14. [4c] C. D. Apostolopoulos, E. A. Couladouros, M. P. Georgiadis, Liebigs Ann. 1994, 781-784.
15. E. A. Couladouros, Z. F. Plyta, S. A. Haroutounian, V. P. Papageorgiou, J. Org. Chem. 1997, 62, 6-10.
16. [6a] M. P. Georgiadis, S. A. Haroutounian, J. C. Bailar, J. Heterocycl. Chem. 1988, 25, 995-1002.
17. [6b] M. P. Georgiadis, A. Tsekouras, S. I. Kotretsou, S. A. Haroutounian, M. G. Polissiou, Synthesis 1991, 929-932.
18. T. Nakazawa, T. Suzuki, M. Ishii, Tetrahedron Lett. 1997, 38, 8951-8954.
19. [8a] J. V. Greenhill, Chem. Soc. Rev. 1977, 6, 277-297.
20. [8b] A. Alberola, J. M. Andres, A. Gonzalez, R. Pedrosa. M. Vincente, Heterocycles 1990, 31, 1049-1058.
21. [9a] Y. Tamura, K. Sumoto, H. Matsushima, H. Taniguchi, M. Ikeda, J. Org. Chem. 1973, 38, 4324-4328.
22. [9b] N. Furukawa, T. Yoshimura, M. Ohtsu, T. Akasaka, S. Oae, Tetrahedron 1980, 36, 73-80.
23. J. J. Bozell, L. S. Hegedus, J. Org. Chem. 1981, 46, 2561-2563.
24. T. Hosokawa, M. Takano, Y. Kuroki, S-I. Murahashi, Terahedron Lett. 1992, 33, 6643-6646.
25. S. Seko, N. Tani, Tetrahedron Lett. 1998, 39, 8117-8120.
26. S-I. Murahashi, S. Sasao, E. Saito, T. Naota, Tetrahedron 1993, 49, 8805-8826.
27. [14a] O. Jr. Achmatowicz, P. Bukowski, B. Szechner, Z. Swierzchowska, A. Zamojski, Terahedron 1971, 27, 1973-1996.
28. [14b] Y. Lefebvre, Terahedron Lett. 1972, 36, 4983-4984.
29. [14c] W. S. Zhou, Z. H. Lu, Z. M. Wang, Terahedron Lett. 1991, 32, 1467-1470.
30. [14d] W. S. Zhou, Z. H. Lu, Z. M. Wang, Terahedron 1993, 49, 2641-2654.
31. [14e] H.-J. Altenbach, R. Wischnat, Tetrahedron Lett. 1995, 36, 4983-4984.
32. L. F. Fieser, J. L. Hartwell, J. Am. Chem. Soc. 1935, 57, 1482-1488.
33. F. Effenberger, T. Beisswenger, Chem. Ber. 1984, 118, 4869-4876.
34. 4; see: Org. React. 1949, 3, 327.
35. G. Chelucci, M. A. Cabras, A. Saba, Tetrahedron: Asymmetry 1994, 5, 1973-1978.
36. 2O; see: L. M. Fieser, M. Fieser, Reagents for Organic Synthesis, John Wiley & Sons Inc., New York, 1967, p. 142.