3-Ylidenepiperazine-2,5-diones as versatile organic substrates

Abstract

3-Ylidenepiperazine-2,5-diones and 3,6-diylidenepiperazine-2,5-diones are cyclic dipeptides consisting of one or two didehydroamino acid moieties, respectively. Some compounds of this series occur in nature. They can easily be synthesised by several methods also in optically active form and are prone to addition reactions to the C–C double bond by electrophiles (enamine reactivity), nucleophiles (Michael reactivity), radicals, oxidising reagents or 1,3-dipoles, usually in a stereoselective manner. The resulting adducts can further be transformed to natural products and analogues or serve as precursors for interesting α-amino or α-keto acid derivatives by cleavage of the diketopiperazine ring.

References

1. P. G. Sammes, Prog. Chem. Org. Nat. Prod., 1975, 32, 51.
2. H. Poisel and U. Schmidt, Chem. Ber., 1973, 106, 3408.
3. S. D. Bull, S. G. Davies and M. D. O'Shea, J. Chem. Soc., Perkin Trans. 1, 1998, 3657.
4. C. Shin, Heterocycles, 1983, 20, 1407.
5. D. Person and M. le Corre, Bull. Soc. Chim. Fr., 1989, 673.
6. A. Lieberknecht and H. Griesser, Tetrahedron Lett., 1987, 28, 4275.
7. C. Gallina and A. Liberatori, Tetrahedron, 1974, 30, 667.
8. K. Itoh, M. Kasami, R. Yamada, T. Kubo, M. Honda and A. Sera, Heterocycles, 1997, 45, 1345.
9. N. Saito, K. Tashiro, Y. Maru, K. Yamaguchi and A. Kubo, J. Chem. Soc., Perkin Trans. 1, 1997, 53.
10. Y. Sato, Y. Nakajima and C. Shin, Heterocycles, 1992, 33, 589.
11. M. Yamaura, T. Suzuki, H. Hashimoto, J. Yoshimura and C. Shin, Bull. Chem. Soc. Jpn., 1985, 58, 2812.
12. C. L. L. Chai and A. R. King, Tetrahedron Lett., 1995, 36, 4295.
13. M. Bergmann and A. Miekeley, Liebigs Ann. Chem., 1927, 458, 40.
14. K. H. Ongania, Arch. Pharm. (Weinheim, Ger.), 1979, 312, 963.
15. S. M. Marcuccio and J. A. Elix, Aust. J. Chem., 1985, 38, 1785.
16. J. D. M. Herscheid, H. P. H. Scholten, M. W. Tijhuis and H. C. J. Ottenheijm, Recl. Trav. Chim. Pays-Bas, 1981, 100, 73.
17. J. A. Marshall, T. F. Schlaf and J. G. Csernansky, Synth. Commun., 1975, 5, 237.
18. W.-R. Li and S.-Z. Peng, Tetrahedron Lett., 1998, 39, 7373.
19. M. Nakagawa, H. Fukushima, T. Kawate, M. Hongu, T. Une, S. I. Kodato, M. Taniguchi and T. Hino, Chem. Pharm. Bull., 1989, 37, 23.
20. P. J. Machin and P. G. Sammes, J. Chem. Soc., Perkin Trans. 1, 1974, 698.
21. K. W. Blake and P. G. Sammes, J. Chem. Soc. (C), 1970, 980.
22. S. Jin and J. Liebscher, Synlett, 1999, 459.
23. M. Oba, S. Nakajima and K. Nishiyama, Chem. Commun., 1996, 16, 1875.
24. S. Jin and J. Liebscher, J. Prakt. Chem., 1998, 340, 390.
25. M. A. F. Elkaschef, K. E. Mokhtar, F. M. E. Abdel-Megeid and S. A. A. Khallaf, J. Chem. Soc. (C), 1969, 622.
26. Y. Kishi, S. Nakatsuka, T. Fukuyama and M. Havel, J. Am. Chem. Soc., 1973, 95, 6493.
27. A. Bartels, S. Jin and J. Liebscher, unpublished results, see also A. Bartels, Dissertation, Humboldt-University Berlin, 1997 and S. Jin, Dissertation, Humboldt-University Berlin, 1999 under preparation.
28. J. Moyroud, J. Gelin, A. Chene and J. Mortier, Tetrahedron, 1996, 52, 8525.
29. J. Yoshimura, Y. Sugiyama and H. Nakamura, Bull. Chem. Soc. Jpn., 1973, 46, 2850.
30. C. Shin, Y. Sato, S. Honda and J. Yoshimura, Bull. Chem. Soc. Jpn., 1983, 56, 2652.
31. T. Fukuyama, B. D. Robins and R. A. Sachleben, Tetrahedron Lett., 1981, 22, 4155.
32. Y. S. Oh and H. Kohn, J. Org. Chem., 1992, 57, 3662.
33. S. I. Nakatsuka, K. Teranishi and T. Goto, Tetrahedron Lett., 1986, 27, 6361.
34. S. I. Kodato, M. Nakagawa, M. Hongu, T. Kawate and T. Hino, Tetrahedron, 1988, 44, 359.
35. P. J. Machin and P. G. Sammes, J. Chem. Soc., Perkin Trans. 1, 1976, 628.
36. A. Bartels, P. G. Jones and J. Liebscher, Tetrahedron Lett., 1995, 36, 3673.
37. C. Alcaraz, M. D. Fernandez, M. P. deFrutos, J. L. Marco and M. Bernabe, Tetrahedron, 1994, 50, 12443.