Synthesis of N-alkoxycarbonyl-3-substituted tetramic acids and functionalized enols via C-acylation reactions of active methylene compounds with N-hydroxysuccinimide esters of N-alkoxycarbonyl-α-amino acids

Abstract

The N-hydroxysuccinimide esters of N-alkoxycarbonyl-α-amino acids react with active methylene compounds (malonic and acyl acetic esters), under basic conditions, to produce N-alkoxycarbonyl-3-substituted tetramic acids 7–17; in the case of the N-hydroxysuccinimide ester of L-alanine, the corresponding optically active tetramic acids 15 and 16 are obtained. In addition, the C-acylation reactions of cyanoacetic esters furnishes the functionalized enols 18–23 in very good yields. Spectral data and physical characteristics for all compounds are reported.

References

1. B. J. L. Royles, Chem. Rev., 1995, 95, 1981.
2. R. N. Lacey, J. Chem. Soc., 1954, 850.
3. T. P. C. Mulholland, R. Foster and D. B. Haydock, J. Chem. Soc., Perkin Trans. 1, 1972, 17, 2121.
4. R. K. Boeckman, Jr. and A. J. Thomas, J. Org. Chem., 1982, 47, 2823; S. V. Ley, S. C. Smith and P. R. Woodward, Tetrahedron Lett., 1988, 29, 5829.
5. (a) R. C. F. Jones and J. M. Patience, Tetrahedron Lett., 1989, 30, 3217; (b) R. C. F. Jones, G. Bhalay, P. A. Carter, K. A. M. Duller and S. I. E. Vulto, J. Chem. Soc., Perkin Trans. 1, 1994, 2513.
6. P. DeShong, J. A. Cipollina and N. K. Lownmaster, J. Org. Chem., 1988, 53, 1356.
7. S. V. Ley, S. C. Smith and P. R. Woodward, Tetrahedron, 1992, 48, 1145.
8. R. K. Boeckman, Jr., C. H. Weidner, R. B. Perni and J. J. Napier, J. Am. Chem. Soc., 1989, 111, 8036.
9. L. A. Paquette, D. Macdonald, L. G. Anderson and J. Wright, J. Am. Chem. Soc., 1989, 111, 8037.
10. R. C. F. Jones and M. Tankard, J. Chem. Soc., Perkin Trans. 1, 1991, 240.
11. J.-A. Fehrentz, E. Bourdel, J.-C. Califano, O. Chaloin, C. Devin, P. Garrouste, A.-C. Lima-Leite, M. Llinares, F. Rieunier, J. Vizavonna, F. Winternitz, A. Loffet and J. Martinez, Tetrahedron Lett., 1994, 35, 1557; J. J. Leban and K. L. Colson, J. Org. Chem., 1996, 61, 228.
12. P. Jouin, B. Castro and D. Nisato, J. Chem. Soc., Perkin Trans. 1, 1987, 1177; N. Galeotti, J. Poncet, L. Chiche and P. Jouin, J. Org. Chem., 1993, 58, 5370; U. Schmidt, B. Riedl, G. Haas, H. Griesser, A. Vetter and S. Weinbrenner, Synthesis, 1993, 216.
13. (a) G. Sauvé, N. Le Berre and B. Zacharie, J. Org. Chem., 1990, 55, 3002; (b) M. Vaillancourt, B. Vanasse, E. Cohen and G. Sauve, Bioorg. Med. Chem. Lett., 1993, 3, 1169.
14. O. Igglessi-Markopoulou and C. Sandris, J. Heterocycl. Chem., 1982, 19, 883; O. Igglessi-Markopoulou and C. Sandris, J. Heterocycl. Chem., 1985, 22, 1599; O. Markopoulou, J. Markopoulos and D. Nicholls, J. Inorg. Biochem., 1990, 39, 307.
15. A. Detsi, J. Markopoulos and O. Igglessi-Markopoulou, Chem. Commun., 1996, 1323.
16. G. W. Anderson, J. E. Zimmermann and F. M. Callahan, J. Am. Chem. Soc., 1964, 86, 1839.
17. S. Forsén, F. Merényi and M. Nilsson, Acta Chem. Scand., 1964, 18, 1208.
18. J. B. Stothers and P. C. Lauterbur, Can. J. Chem., 1964, 42, 1563.
19. P. S. Steyn and P. L. Wessels, Tetrahedron Lett., 1978, 47, 4707; M. J. Nolte, P. S. Steyn and P. L. Wessels, J. Chem. Soc., Perkin Trans. 1, 1980, 1057.
20. J. V. Barkley, J. Markopoulos and O. Igglessi-Markopoulou, J. Chem. Soc., Perkin Trans. 2, 1994, 1271.
21. (a) J. L. Burdett and M. T. Rogers, J. Am. Chem. Soc., 1964, 86, 2105; (b) C. F. G. C. Geraldes, M. T. Barros, C. D. Maycock and M. I. Silva, J. Mol. Struct., 1990, 238, 335.