Spiroheterocycles from reaction of nitrones with methylene-γ-butyrolactones and some of their rearrangements

Organic and Biomolecular Chemistry

Volumn 1, Issue 15, 2003, Pages 2689-2698

  Roussel, Christophe ^a,e   Fihi, Rachid ^b   Ciamala, Kabula ^a   Vebrel, Joël ^a   Zair, Touria ^c   Riche, Claude ^d  

^a Lab de Chim des Mat et Interfaces   (France)

^b MOULAY ISMAIL UNIVERSITY   (Morocco)

^c MOULAY ISMAIL UNIVERSITY   (Morocco)

^d CNRS   (France)

^e Institut de chimie moleculaire et biologique Ecole Polytechnique Federale de Lausanne   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; ALKALINITY; ISOMERS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

ALKALINE MEDIA;

REACTION KINETICS;

EID: 0141618491     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b300628j     Document Type: Article

References (42)

1. R. Fihi, K. Ciamala, J. Vebrel and N. Rodier, Bull. Soc. Chim. Belg., 1995, 104, 55.
2. C. Roussel, R. Fihi, K. Ciamala, P. Audebert and J. Vebrel, New J. Chem., 2000, 24, 471.
3. R. K. Howe, B. R. Shelton and K. C. Liu, J. Org. Chem., 1985, 50, 903.
4. R. K. Howe and B. R. Shelton, J. Org. Chem., 1990, 55, 4603.
5. M. C. Aversa, G. Cum, G. Stagno d'Alcontres and N. Uccella, J. Chem. Soc., Perkin Trans. 1, 1972, 222.
6. A. Kerbal, J. Vebrel, M. Roche and B. Laude, Tetrahedron Lett., 1990, 31, 4145.
7. M. Msaddek, M. Rammah, G. Schmitt and J. Vebrel, Bull. Soc. Chim. Belg., 1992, 101, 323.
8. M. Msaddek, M. Rammah, K. Ciamala, J. Vebrel and B. Laude, Synthesis, 1997, 1495.
9. K. C. Liu and R. K. Howe, J. Org. Chem., 1983, 48, 4590.
10. C. Roussel, K. Ciamala, P. Audebert and J. Vebrel, New J. Chem., 1999, 23, 989.
11. J. Nadelson, U. S. Pat. 3,987,179 (Chem. Abstr., 1976, 85, 143087z).
12. J. Nadelson, U. S. Pat. 3,987,179 (Chem. Abstr., 1976, 85, 143087z).
13. J. Nadelson, U. S. Pat, 4,032,644 (Chem. Abstr., 1977, 87, 102314u).
14. J. Nadelson, U. S. Pat, 4,032,644 (Chem. Abstr., 1977, 87, 102314u).
15. R. L. N. Harris and J. L. Huppatz, Aunt. J. Chem., 1977, 30, 2225.
16. Commonwealth Scientific and Industrial Research Organization, German Patent 2600655 (Chem. Abstr., 1976, 85, 155072d).
17. Commonwealth Scientific and Industrial Research Organization, German Patent 2600655 (Chem. Abstr., 1976, 85, 155072d).
18. R. K. Howe, U. S. Pat. 4,229,204 (Chem. Abstr., 1981, 94, 84101k).
19. R. K. Howe, U. S. Pat. 4,229,204 (Chem. Abstr., 1981, 94, 84101k).
20. R. K. Howe and K. C. Liu, U. S. Pat. 971,462 (Chem. Abstr., 1981, 94, 47311h).
21. R. K. Howe and K. C. Liu, U. S. Pat. 971,462 (Chem. Abstr., 1981, 94, 47311h).
22. D. Alonso-Perarnau, P. De March, M. El Arrad, M. Figueredo, J. Font and T. Parella, Tetrahedron, 1997, 53, 14763.
23. M. Cacciarini, F. M. Cordero, C. Faggi and, A. Goti, Molecules, 2000, 5, 637.
24. E. Shaw, J. Am. Chem. Soc., 1946, 68, 2510.
25. S. Rigolet, P. Goncalo, J. M. Mélot and J. Vebrel, J. Chem. Res., 1998, (M)2813.
26. S. Rigolet, J. M. Mélot, J. Vebrel, A. Chiaroni and C. Riche, J. Chem. Soc., Perkin Trans. 1, 2000, 1095.
27. K. B. G. Torsseil, in Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis, ed. H. Feuer, VCH Publishers, New York, 1988.
28. R. Grée and R. Carrié, Tetrahedron Lett., 1971, 4117.
29. M. Masui, K. Suda, M. Yamauchi and C. Yijima, Chem. Pharm. Bull., 1973, 21, 1605.
30. M. Joucla, D. Grée and J. Hamelin, Tetrahedron, 1973, 29, 2315.
31. A. Vasella, Helv. Chim. Acta, 1977, 60, 426.
32. A. Padwa, U. Chiacchio, D. N. Kline and J. Perumattan, J. Org. Chem., 1988, 53, 2238.
33. A. Liguori, G. Romeo, G. Sindona and N. Uccella, Gazz. Chim. Ital., 1991, 121, 393.
34. F. Casuscelli, U. Chiacchio, A. Rescifina, R. Romeo, G. Romeo, S. Tommasini and N. Uccella, Tetrahedron, 1995, 51, 2979.
35. G. M. Sheldrick, Acta Crystallogr., Sect A: Fundam. Crystallogr., 1990, 46, 467.
36. G. M. Sheldrick, SHELXL93, Program for the refinement of crystal structures, University of Göttingen, Germany, 1993.
37. CCDC reference number 167244, See http://www.rsc.org/suppdata/ob/b3/b300628j/ for crystallographic data in .cif or other electronic format.
38. R. A. Amos and J. A. Katzenellenbogen, J. Org. Chem., 1978, 43, 560.
39. C. Grundmann and E. Kober, J. Am. Chem. Soc., 1955, 77, 2332.
40. I. Brüning, R. Grashey, H. Hauck, R. Huisgen and H. Seidl, Org. Synth. Coll. Vol. V, 1124.
41. R. M. Cowper and L. H. Davidson, Org. Synth. Coll. Vol. II, 480.
42. F. Kröhnke and E. Börner, Chem. Ber., 1936, 69, 2006.