A Simple Synthesis of β-Amino Sulfides

Synlett

Volumn 1997, Issue 8, 1997, Pages 915-916

  Ishibashi, Hiroyuki ^a   Uegaki, Masayuki ^a   Sakai, Manami ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000534361     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-971     Document Type: Article

References (39)

1. (a) Leyendecker, F.; Laucher, D. Tetrahedron Lett. 1983, 24, 3517.
2. (b) Leyendecker, F.; Laucher, D. Nouv. J. Chim. 1985, 9, 13.
3. (c) Dieter, R.K.; Tokles, M. J. Am. Chem. Soc. 1987, 109, 2040.
4. (d) Davies, I.W.; Gallagher, T.; Lamont, R.B.; Scopes, D.I.C. J. Chem. Soc., Chem. Commun. 1992, 335.
5. (e) Takano, S.; Iida, H.; Inomata, K.; Ogasawara, K. Heterocycles 1993, 35, 47.
6. (f) Hof, R.P.; Poelert, M.A.; Peter, N.C.M.W.; Kellog, R.M. Tetrahedron: Asymmetry 1994, 5, 31.
7. (g) Kang, J.; Kim, D.S.; Kim, J.I. Synlett 1994, 842.
8. (h) Matsuo, K.; Arase, T. Chem. Pharm. Bull. 1995, 43, 2091.
9. (i) Donner, B.G. Tetrahedron Lett. 1995, 36, 1223.
10. (j) Gibson, C.L. Tetrahedron: Asymmetry 1996, 7, 3357.
11. (k) Shinohara, T.; Toda, J.; Sano, T. Chem. Pharm. Bull. 1997, 45, 813.
12. (a) Tank, L.I. Med. Radiol. 1961, 6, 76; Chem. Abstr. 1962, 56, 7664f.
13. (a) Tank, L.I. Med. Radiol. 1961, 6, 76; Chem. Abstr. 1962, 56, 7664f.
14. (b) Commercial Solvents Corp. Neth. Patent 6404644, 1964 ;Chem. Abstr. 1965, 62, 16131c.
15. (c) Tucker, H.; Coope, J.F. J. Med. Chem. 1978, 21, 769.
16. (d) Relenyi, A.G.; Walter, R.W.; Gartner, C.D. U.S. Patent 5118534, 1992; Chem. Abstr. 1992, 117, 89850g.
17. (e) Tomkins, J.M.; Barnes, K.J.; Blacker, A.J.; Watkins, W.J.; Abell, C. Tetrahedron Lett. 1997, 38, 691.
18. (a) Lehr, H.; Karlan, S.; Goldberg, M.W. J. Med. Chem. 1963, 6, 136.
19. (b) Wehrmeister, H.L. J. Org. Chem. 1963, 28, 2589.
20. (c) Bewick, A.; Mellor, J.M.; Owton, W.M. J. Chem. Soc., Perkin Trans, 1 1985, 1039.
21. (d) Poindexter, G.S.; Owens, D.A.; Dolan, P.L.; Woo, E. J. Org. Chem. 1992, 57, 6257.
22. (e) Osborn, H.M.I.; Sweeney, J.B. Synlett 1994, 145.
23. (f) Cran, G.A.; Gibson, C.L.; Handa, S. Tetrahedron: Asymmetry 1995, 6, 1553.
24. (g) Orlek, B.S. Synlett 1996, 477.
25. (h) Siedlecka, R.; Skarzewski, J. Synlett 1996, 757.
26. (i) Hayashi, M.; Ono, K.; Hoshimi, H.; Oguni, N. Tetrahedron 1996, 52, 7817.
27. Hata, Y.; Watanabe, M.; Shiratori, O.; Takase, S. Biochem. Biophys. Res. Commun. 1978, 80, 911. Fishbein, L.J. Toxicol. Environ. Health (U.S.A.) 1980, 6, 1133.
28. Hata, Y.; Watanabe, M.; Shiratori, O.; Takase, S. Biochem. Biophys. Res. Commun. 1978, 80, 911. Fishbein, L.J. Toxicol. Environ. Health (U.S.A.) 1980, 6, 1133.
29. Poindexter and his coworkers reported that heating a mixure of 2-oxazolidinone (1) and aromatic thiols at 150°C without a solvent provided 2-(arylthio)ethylamines in moderate yields (27-66%). It was suggested that the reaction involves a protonation on the carbonyl oxygen atom of 1 with the aid of acidic aromatic thiols, so that the aliphatic thiols such as octanethiol gives no corresponding aminoethyl sulfides. See ref. 3d.
30. Several examples of the cleavage of the C-O bond of the alkoxy group with thiolate anions have been reported. For esters, see: Bartlett, P.A.; Johnson, W.S. Tetrahedron Lett. 1970, 4459. For lactones, see: Plieninger, H. Chem. Ber. 1950, 83, 265. For ethylene carbonates, see: Tamura, Y.; Saito, T.; Ishibashi, H.; Ikeda, M. Synthesis 1975, 641.
31. Several examples of the cleavage of the C-O bond of the alkoxy group with thiolate anions have been reported. For esters, see: Bartlett, P.A.; Johnson, W.S. Tetrahedron Lett. 1970, 4459. For lactones, see: Plieninger, H. Chem. Ber. 1950, 83, 265. For ethylene carbonates, see: Tamura, Y.; Saito, T.; Ishibashi, H.; Ikeda, M. Synthesis 1975, 641.
32. Several examples of the cleavage of the C-O bond of the alkoxy group with thiolate anions have been reported. For esters, see: Bartlett, P.A.; Johnson, W.S. Tetrahedron Lett. 1970, 4459. For lactones, see: Plieninger, H. Chem. Ber. 1950, 83, 265. For ethylene carbonates, see: Tamura, Y.; Saito, T.; Ishibashi, H.; Ikeda, M. Synthesis 1975, 641.
33. Compound 3 is assumed to be in equilibrium with 1 and EtONa under the reaction conditions. Indeed, treatment of 3 with EtONa (2 equiv.) in refluxing EtOH for 30 min gave a mixture of 3 and 1 in a ratio of approximately 1.3:1.
34. It is of interest that the compound which might arise from nucleophilic attack of amine 2a on the carbonyl carbon atom of 1 did not detected in the crude reaction mixture. This may be ascribed to the lower nucleophilicity of amine 2a compared to benzenethiolate and ethoxide anions. Even when a mixture of stoichiometric amounts of 2a and 1 was heated in boiling EtOH for 24 h. only a trace amount of N-(2-phenylthioethyl)-(N'-(2-hydroxyethyl)urea was formed.
35. All yields herein described are based on 2-oxazolidinones.
36. All new compounds gave satisfactory elemental analyses and spectroscopic data.
37. D value for 2e is not indicated in ref. 3e.
38. Aoyagi, Y.; Manabe, T.; Ohta, A.; Kurihara, T.; Pang, G.-L., Yuhara, T. Tetrahedron 1996, 52, 869.
39. When a similar reaction was carried out by using Method B (in refluxing tert-BuOH), the yield of 9 was only a 18% yield.