Aromatic or chiral heterocycle - Balance between 1,3-oxazoline-2-thione and 1,3-oxazolidine-2-thione

Synlett

Volumn , Issue 2, 2006, Pages 301-305

  Leconte, Nicolas ^a   Silva, Sandrina ^a,b   Tatibouët, Arnaud ^a   Rauter, Amelia P ^b   Rollin, Patrick ^a  

^a UNIVERSITÉ D'ORLÉANS   (France)

^b UNIVERSITY OF LISBON   (Portugal)

Author keywords

1,3 oxazol idine 2 thione; 1,3 oxazoline 2 thione; Hydroxyketones

Indexed keywords

1,3 OXAZOLIDINE 2 THIONE; 1,3 OXAZOLINE 2 THIONE; HETEROCYCLIC COMPOUND; KETOL; OXAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; HYDROLYSIS; OXIDATION; REACTION ANALYSIS; RING OPENING; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 32344442319     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-923583     Document Type: Article

References (29)

1. Velazquez, F.; Olivo, H. F. Curr. Org. Chem. 2002, 6, 1.
2. (a) Crimmins, M. T.; King, B. W.; Zuercher, W. J.; Choy, A. L. J. Org. Chem. 2000, 65, 8499.
3. (b) Crimmins, M. T.; Zuercher, W. J. Org. Lett. 2000, 2, 1065.
4. (c) Crimmins, M. T.; Tabet, E. A. J. Org. Chem. 2001, 66, 4012.
5. (d) Chakraborty, T. K.; Jayaprakash, S.; Laxman, P. Tetrahedron 2001, 57, 9461.
6. (e) Crimmins, M. T.; Katz, J. D.; Washburn, D. G.; Allwein, S. P.; McAtee, L. F. J. Am. Chem. Soc. 2002, 124, 5661.
7. (a) Gueyrard, D.; Grumel, V.; Leoni, O.; Palmieri, S.; Rollin, P. Heterocycles 2000, 52, 827.
8. (b) Leoni, O.; Bernardi, R.; Gueyrard, D.; Rollin, P.; Palmieri, S. Tetrahedron: Asymmetry 1999, 10, 4775.
9. (a) Zemplen, G.; Gerecs, A.; Rados, M. Ber. Dtsch. Chem. Ges. B. 1936, 39, 748.
10. (b) Bromund, W. H.; Herbst, R. M. J. Org. Chem. 1945, 10, 267.
11. (c) Garcia Fernandez, J. M.; Ortiz Mellet, C. Sulfur Rep. 1996, 19, 61.
12. (d) Diaz Perez, V. M.; Garcia Moreno, M. I.; Ortiz Mellet, C.; Fuentes, J.; Diaz Arribas, J. C.; Canada, F. J.; Garcia Fernandez, J. M. J. Org. Chem. 2000, 65, 136.
13. (e) Garcia Fernandez, J. M.; Ortiz Mellet, C. Adv. Carbohydr. Chem. Biochem. 2000, 55, 35.
14. Tatibouët, A.; Lawrence, S.; Rollin, P.; Holman, G. D. Synlett 2004, 1945.
15. Saul, R.; Kern, T.; Kopf, J.; Pinter, I.; Köll, P. Eur. J. Org. Chem. 2000, 205.
16. (a) Willems, J. F.; Vandenberghe, A. Bull. Soc. Chim. Belg. 1961, 70, 745.
17. (b) Lacasse, G.; Muchowki, J. M. Can. J. Chem. 1972, 50, 3082.
18. Cioci, G.; Leconte, N.; Tatibouët, A.; Rollin, P.; Pérez, S.; Imberty, A. Acta Crystallogr., Sect. E 2004, o2399.
19. Nedolya, N. A.; Papsheva, N. P.; Afonin, A. V.; Trofimov, B. A.; Kukhareva, V. A.; Kashik, T. V. Sulfur Lett. 1992, 14, 103.
20. (a) Bradscher, C. K.; Jones, W. J. J. Org. Chem. 1967, 32, 2079.
21. (b) Guimon, C.; Pfister-Guillouzo, G.; Arbelot, M.; Chanon, M. Tetrahedron 1974, 30, 3831.
22. (c) Kapsomenos, G. S.; Akrivos, P. D. Can. J. Chem. 1988, 66, 2835.
23. (d) Shafer, C. M.; Molinski, T. F. J. Org. Chem. 1998, 63, 551.
24. Casarotti, E.; Antognazza, P.; Pallavicini, M.; Villa, L. Helv. Chim. Acta 1993, 76, 2344.
25. (a) Lichtenthaler, F. W.; Doleschal, W.; Hahn, S. Liebigs Ann. Chem. 1985, 2454.
26. (b) Tatibouët, A.; Lefoix, M.; Nadolny, J.; Martin, O. R.; Rollin, P.; Yang, J.; Holman, G. D. Carbohydr. Res. 2001, 333, 327.
27. (a) Girniene, J.; Gueyrard, D.; Tatibouët, A.; Sackus, A.; Rollin, P. Tetrahedron Lett. 2001, 42, 2977.
28. (b) Girniene, J.; Tatibouët, A.; Sackus, A.; Yang, J.; Holman, G. D.; Rollin, P. Carbohydr. Res. 2003, 338, 711.
29. (c) Girniene, J.; Tardy, S.; Tatibouët, A.; Sackus, A.; Rollin, P. Tetrahedron Lett. 2004, 45, 6443.