Studies on the reactivity of N-(3-thienyl)carbamates

Journal of the Chemical Society. Perkin Transactions 1

Volumn , Issue 1, 2001, Pages 37-43

  Brugier, Delphine ^a   Outurquin, Francis ^a   Paulmier, Claude ^a  

^a UNIVERSITÉ DE ROUEN   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; CATALYSIS; CHELATION; FREE RADICALS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

CYCLIZATION REACTIONS;

ORGANOMETALLICS;

EID: 0035819445     PISSN: 14727781     EISSN: None     Source Type: Journal    
DOI: 10.1039/b003580g     Document Type: Article

References (40)

1. I.W. Southon and J. Buckingham, Dictionary of Alkaloids, Chapman and Hall, London, 1989. ed. J.E. Saxton, Chem. Heterocycl. Compd., 1994, 25, Suppl. IV; K.C. Joshi and P. Chand, Pharmazie, 1982, 37, 1.
2. I.W. Southon and J. Buckingham, Dictionary of Alkaloids, Chapman and Hall, London, 1989. ed. J.E. Saxton, Chem. Heterocycl. Compd., 1994, 25, Suppl. IV; K.C. Joshi and P. Chand, Pharmazie, 1982, 37, 1.
3. F. Garcia and C. Galvez, Synthesis, 1985, 143.
4. C. Paulmier, Sulfur Rep., 1996, 19, 215.
5. W.W. Gale, A.N. Scott and H.R. Snider, J. Org. Chem., 1964, 29, 2160; S. Soth, M. Farnier and C. Paulmier, Can. J. Chem., 1978, 56, 1429; C. Galvez and F. Garcia, J. Heterocycl. Chem., 1984, 21, 393.
6. W.W. Gale, A.N. Scott and H.R. Snider, J. Org. Chem., 1964, 29, 2160; S. Soth, M. Farnier and C. Paulmier, Can. J. Chem., 1978, 56, 1429; C. Galvez and F. Garcia, J. Heterocycl. Chem., 1984, 21, 393.
7. W.W. Gale, A.N. Scott and H.R. Snider, J. Org. Chem., 1964, 29, 2160; S. Soth, M. Farnier and C. Paulmier, Can. J. Chem., 1978, 56, 1429; C. Galvez and F. Garcia, J. Heterocycl. Chem., 1984, 21, 393.
8. (a) D. Wensbo, A. Eriksson, T. Jeschke, U. Annby, S. Gronowitz and L.A. Cohen, Tetrahedron Lett., 1993, 34, 2823.
9. (b) D. Wensbo, U. Annby and S. Gronowitz, Tetrahedron, 1995, 51, 10323.
10. (c) D. Wensbo and S. Gronowitz, Tetrahedron, 1996, 52, 14975.
11. C. Galvez, F. Garcia, A. Marzal and P. Viladoms, J. Chem. Res., 1994, 12; D.N. Reinhoudt, J. Geevers, W.P. Trompenaars, S. Harkema and G.J. Van Hummel, J. Org. Chem., 1981, 46, 424.
12. C. Galvez, F. Garcia, A. Marzal and P. Viladoms, J. Chem. Res., 1994, 12; D.N. Reinhoudt, J. Geevers, W.P. Trompenaars, S. Harkema and G.J. Van Hummel, J. Org. Chem., 1981, 46, 424.
13. (a) F. Outurquin and C. Paulmier, Bull. Soc. Chim. Fr., 1983, II, 153; F. Outurquin and C. Paulmier, Bull. Soc. Chim. Fr., 1983, II, 159.
14. (a) F. Outurquin and C. Paulmier, Bull. Soc. Chim. Fr., 1983, II, 153; F. Outurquin and C. Paulmier, Bull. Soc. Chim. Fr., 1983, II, 159.
15. (b) F. Outurquin, P. Lerouge and C. Paulmier, Bull. Soc. Chim. Fr., 1986, 259; F. Outurquin, P. Lerouge and C. Paulmier, Bull. Soc. Chim. Fr., 1986, 267.
16. (b) F. Outurquin, P. Lerouge and C. Paulmier, Bull. Soc. Chim. Fr., 1986, 259; F. Outurquin, P. Lerouge and C. Paulmier, Bull. Soc. Chim. Fr., 1986, 267.
17. (c) F. Outurquin and C. Paulmier, Tetrahedron Lett., 1993, 34, 5715.
18. (d) M. Berkaoui, F. Outurquin and C. Paulmier, J. Heterocycl. Chem., 1996, 33, 9.
19. (e) D. Brugier, F. Outurquin and C. Paulmier, Tetrahedron, 1997, 53, 10331.
20. D. Brugier, F. Outurquin and C. Paulmier, Tetrahedron, 2000, 56, 2985.
21. M.S. Yu, L. Lopez de Leon, M.A. McGuire and G. Bothon, Tetrahedron Lett., 1998, 39, 9347; S. Cacchi, G. Fabrizi, F. Marinelli, L. Moro and P. Pace, Synlett, 1997, 1363; S. Cacchi, G. Fabrizi and P. Pace, J. Org. Chem., 1998, 63, 1001.
22. M.S. Yu, L. Lopez de Leon, M.A. McGuire and G. Bothon, Tetrahedron Lett., 1998, 39, 9347; S. Cacchi, G. Fabrizi, F. Marinelli, L. Moro and P. Pace, Synlett, 1997, 1363; S. Cacchi, G. Fabrizi and P. Pace, J. Org. Chem., 1998, 63, 1001.
23. M.S. Yu, L. Lopez de Leon, M.A. McGuire and G. Bothon, Tetrahedron Lett., 1998, 39, 9347; S. Cacchi, G. Fabrizi, F. Marinelli, L. Moro and P. Pace, Synlett, 1997, 1363; S. Cacchi, G. Fabrizi and P. Pace, J. Org. Chem., 1998, 63, 1001.
24. J. Fujiwara, Y. Fukutani, H. Sano, K. Maruoka and H. Yamamoto, J. Am. Chem. Soc., 1983, 105, 7177; T. Nishikawa, M. Ishikawa and M. Isobe, Synlett, 1999, 123.
25. J. Fujiwara, Y. Fukutani, H. Sano, K. Maruoka and H. Yamamoto, J. Am. Chem. Soc., 1983, 105, 7177; T. Nishikawa, M. Ishikawa and M. Isobe, Synlett, 1999, 123.
26. Y. Kondo, S. Kojima and T. Sakamoto, Heterocycles, 1996, 43, 2741.
27. (a) W.F. Bailey and X.L. Jiang, J. Org. Chem., 1996, 61, 2596.
28. (b) D. Zhang and L.S. Liebeskind, J. Org. Chem., 1996, 61, 2594.
29. For the preparation of indolines via radical cyclization of N-allyl-anilines see: D.L. Boger, R.M. Garbaccio and Q. Jin, J. Org. Chem., 1997, 62, 8875; J. Inanaga, O. Ujikawa and M. Yamaguchi, Tetrahedron Lett., 1991, 32, 1737; Y. Hayashi, H. Shinokubo and K. Oshima, Tetrahedron Lett., 1998, 39, 63; J. Nakao, R. Inoue, H. Shinokubo and K. Oshima, J Org. Chem., 1997, 62, 1910.
30. For the preparation of indolines via radical cyclization of N-allyl-anilines see: D.L. Boger, R.M. Garbaccio and Q. Jin, J. Org. Chem., 1997, 62, 8875; J. Inanaga, O. Ujikawa and M. Yamaguchi, Tetrahedron Lett., 1991, 32, 1737; Y. Hayashi, H. Shinokubo and K. Oshima, Tetrahedron Lett., 1998, 39, 63; J. Nakao, R. Inoue, H. Shinokubo and K. Oshima, J Org. Chem., 1997, 62, 1910.
31. For the preparation of indolines via radical cyclization of N-allyl-anilines see: D.L. Boger, R.M. Garbaccio and Q. Jin, J. Org. Chem., 1997, 62, 8875; J. Inanaga, O. Ujikawa and M. Yamaguchi, Tetrahedron Lett., 1991, 32, 1737; Y. Hayashi, H. Shinokubo and K. Oshima, Tetrahedron Lett., 1998, 39, 63; J. Nakao, R. Inoue, H. Shinokubo and K. Oshima, J Org. Chem., 1997, 62, 1910.
32. For the preparation of indolines via radical cyclization of N-allyl-anilines see: D.L. Boger, R.M. Garbaccio and Q. Jin, J. Org. Chem., 1997, 62, 8875; J. Inanaga, O. Ujikawa and M. Yamaguchi, Tetrahedron Lett., 1991, 32, 1737; Y. Hayashi, H. Shinokubo and K. Oshima, Tetrahedron Lett., 1998, 39, 63; J. Nakao, R. Inoue, H. Shinokubo and K. Oshima, J Org. Chem., 1997, 62, 1910.
33. D.L. Clive, V. Farina, A. Singh, C.K. Wong, W.A. Kiel and S.M. Menchen, J. Org. Chem., 1980, 45, 2120; K.C. Nicolaou, D.A. Claremon, W.E. Barnette and S.P. Seitz, J. Am. Chem. Soc., 1979, 103, 3703; R.R. Weeb and S. Danishefsky, Tetrahedron Lett., 1983, 24, 1357.
34. D.L. Clive, V. Farina, A. Singh, C.K. Wong, W.A. Kiel and S.M. Menchen, J. Org. Chem., 1980, 45, 2120; K.C. Nicolaou, D.A. Claremon, W.E. Barnette and S.P. Seitz, J. Am. Chem. Soc., 1979, 103, 3703; R.R. Weeb and S. Danishefsky, Tetrahedron Lett., 1983, 24, 1357.
35. D.L. Clive, V. Farina, A. Singh, C.K. Wong, W.A. Kiel and S.M. Menchen, J. Org. Chem., 1980, 45, 2120; K.C. Nicolaou, D.A. Claremon, W.E. Barnette and S.P. Seitz, J. Am. Chem. Soc., 1979, 103, 3703; R.R. Weeb and S. Danishefsky, Tetrahedron Lett., 1983, 24, 1357.
36. M. Tingoli, M. Tiecco, L. Testaferi and A. Temperini, Synth. Commun., 1998, 28, 1769.
37. M. Berkaoui, Thesis, Rouen, 1998.
38. C. Galvez, F. Garcia, J. Garcia and J. Soldevila, J. Heterocycl. Chem., 1986, 23, 1103.
39. F. Garcia and C. Galvez, Sulfur Lett., 1982, 1, 97; E.W. Brunett and W.C. MacCarthy, J. Pharm. Sci., 1968, 57, 2003.
40. F. Garcia and C. Galvez, Sulfur Lett., 1982, 1, 97; E.W. Brunett and W.C. MacCarthy, J. Pharm. Sci., 1968, 57, 2003.