On the synthesis of 5-ethyl Meldrum's acid

Journal of Heterocyclic Chemistry

Volumn 43, Issue 2, 2006, Pages 365-369

  Akué Gédu, Rufine ^a   El Hafidi, Hayate ^a   Rigo, Benoît ^a   Couturier, Daniel ^b  

^a Ecole des Hautes Etudes d'Ingenieur   (France)

^b UNIV LILLE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

5 ETHYL 2,2 DIMETHYL 1,3 DIOXANE 4,6 DIONE; 5 [3 (2,2 DIMETHYL 4,6 DIOXO 1,3 DIOXAN 5 YL)BUTYL] 2,2 DIMETHYL 1,3 DIOXANE 4,6 DIONE; ACETALDEHYDE; DIOXANE DERIVATIVE; MELDRUM ACID; SODIUM BOROHYDRIDE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; REACTION TIME; REDUCTION; SYNTHESIS; TEMPERATURE DEPENDENCE;

EID: 33645215233     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570430217     Document Type: Article

References (38)

1. R. Akué-Gédu, J.-P. Hénichart, D. Couturier and B. Rigo, Tetrahedron Lett., 45, 9197 (2004).
2. For the structure of Meldrum's acid, see A. N. Meldrum, J. Chem. Soc., 93, 598 (1908);
3. D. Davidson and S. A. Bernhard, J. Amer. Chem. Soc., 70, 3426 (1948);
4. For reviews of the chemistry of Meldrum's acid, see [a] H. McNab, Chem. Soc. Rev., 7, 345 (1978);
5. [b] B.-C. Chen, Heterocycles, 32, 529 (1991);
6. [c] F. J. Kunz, P. Margaretha and O. E. Polansky, Chimia, 24, 165 (1970);
7. [d] T. Tsuno and K. Sugiyama, Trends Heterocylic Chem., 7, 91 (2001).
8. For the alkylation of Meldrum's acid [a] under phase transfer conditions: C.-C. Chan and X. Huang, Synthesis, 452 (1982);
9. 3N conditions: B.-C. Chen and P. Lue, Org. Prep. Proc. Int., 24, 185 (1992);
10. [c] under Michael conditions: C.-C. Chan and X. I. A. N. Huang, Synthesis, 224 (1984);
11. [d] under Mitsunobu conditions: T. K. M. Shing, L.-H. Li and K. Narkunan, J. Org. Chem., 62, 1617 (1997);
12. [e] under palladium-catalyzed conditions: B. M. Trost and V. J. Gerusz, J. Amer. Chem. Soc., 117, 5156 (1995).
13. A. D. Wright, M. L. Haslego and F. X. Smith, Tetrahedron Lett., 2325 (1979).
14. P. Margaretha and O. E. Polansky, Tetrahedron Lett., 4983 (1969).
15. F. Bigi, S. Carloni, L. Ferrari, R. Maggi, A. Mazzacani and G. Sartori, Tetrahedron Lett., 42, 5203 (2001).
16. F. E. Ziegler, T. Guenther and R. V. Nelson, Synth. Commun., 10, 661 (1980).
17. F. A. Hedge, C. W. Kruse and H. R. Snyder, J. Org. Chem., 26, 3166 (1961).
18. See also R. Stevenson and J. V. Weber, J. Nat. Prod., 51, 1215 (1988).
19. E. J. Corey, J. Amer. Chem. Soc., 74, 5897 (1952);
20. G. A. Bihlmayer, F. J. Kunz and O. E. Polansky, Monastsch. Chem., 97, 1293 (1966);
21. V. Nair, Synth. Commun, 17, 723 (1987).
22. 3: D. M. Hrubowchak and F. X. Smith, Tetrahedron Lett, 24, 4951 (1983);
23. B. B. Snider and R. B. Smith, Tetrahedron, 58, 25-34 (2002);
24. [b] with ammonium formate: E. Meyer, A. C. Joussef, H. Galmlardo and L. de B. P. de Souza, Synth. Commun, 34, 783 (2004).
25. J. Leitich, P. Schuster and A. Eitel, Tetrahedron, 23, 2221 (1967);
26. P. Schuster, A. Stephen, O. E. Polansky and F. Wessely, Monastsch. Chem., 99, 1246 (1968).
27. M. Eberle and R. G. Lawton, Helv. Chim. Acta, 71, 1974 (1988).
28. 3 reduction: C. F. Nutaitis, R. A. Schultz, J. Obaza, F. X. Smith, J. Org. Chem., 45, 4606 (1980);
29. Sodium borohydride reduction: G. Tóth, T. Tamás and I. Borbély, Synth. Comm., 32, 3659 (2002);
30. B. Hin, P. Majer and T. Tsukamoto, J. Org. Chem., 67, 7365 (2002).
31. [14a] M. T. Crimmins, D. G. Washburn and F. J. Zawacki, Org. Synth., 77, 114 (1999);
32. [b] U. S. Sørensen, E. Falch and P. Krogsgaard-Larsen, J. Org. Chem., 65, 1003 (2000);
33. Y. Oikawa, K. Sugano and O. Yonemitsu, J. Org. Chem., 43, 2087 (1978);
34. D. G. Melillo, I. Shinkai, T. Liu, K. Ryan and M. Sletzinger, Tetrahedron Lett., 2783 (1980);
35. R. P. Houghton, D. J. Lapham, Synthesis, 451 (1982);
36. [c] These conditions give a better result and avoid the use of pyridine as described in literature; they also avoid the formation of a great amount of diethyl malonate: Eastman Kodak Co., US 5,061,799 (1991); Chem. Abstr., 116, 41475r (1992).
37. Compound 1 was obtained from ethyl malonic acid. B. Eistert and F. Geiss, Chem. Ber., 94, 929 (1961).
38. P. Margaretha and O. E. Polansky, Monatsh Chem., 100, 567 (1969).