Mild method for the conversion of amides to thioamides

Journal of Organic Chemistry

Volumn 68, Issue 14, 2003, Pages 5792-5794

  Charette, André B ^a   Grenon, Michel ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATED AMIDES;

ESTERS; HYDROGEN SULFIDE; SUBSTITUTION REACTIONS; SUBSTRATES;

AMMONIUM COMPOUNDS;

AMIDE; AMMONIUM DERIVATIVE; AMMONIUM SULFIDE; HYDROGEN SULFIDE; THIOAMIDE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 0038675618     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0344485     Document Type: Article

References (36)

1. For a recent review on the synthesis of heterocycles from thioamides, see: Jagodzinski, T. S. Chem. Rev. 2003, 103, 197.
2. For reviews on the preparation of thioamides, see: (a) Schaumann, E. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 6; Chapter 2.4, pp 419-434. (b) Bauer, W.; Kühlein, K. In Methoden Org. Chem. 1985, E5, 1218. (c) Walter, W.; Bode, K.-D. Angew. Chem., Int. Ed. Engl. 1966, 5, 447. (d) Hurd, R. N.; De La Mater, G. Chem. Rev. 1961, 61, 45. (e) see also ref 3 and 8.
3. For reviews on the preparation of thioamides, see: (a) Schaumann, E. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 6; Chapter 2.4, pp 419-434. (b) Bauer, W.; Kühlein, K. In Methoden Org. Chem. 1985, E5, 1218. (c) Walter, W.; Bode, K.-D. Angew. Chem., Int. Ed. Engl. 1966, 5, 447. (d) Hurd, R. N.; De La Mater, G. Chem. Rev. 1961, 61, 45. (e) see also ref 3 and 8.
4. For reviews on the preparation of thioamides, see: (a) Schaumann, E. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 6; Chapter 2.4, pp 419-434. (b) Bauer, W.; Kühlein, K. In Methoden Org. Chem. 1985, E5, 1218. (c) Walter, W.; Bode, K.-D. Angew. Chem., Int. Ed. Engl. 1966, 5, 447. (d) Hurd, R. N.; De La Mater, G. Chem. Rev. 1961, 61, 45. (e) see also ref 3 and 8.
5. For reviews on the preparation of thioamides, see: (a) Schaumann, E. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 6; Chapter 2.4, pp 419-434. (b) Bauer, W.; Kühlein, K. In Methoden Org. Chem. 1985, E5, 1218. (c) Walter, W.; Bode, K.-D. Angew. Chem., Int. Ed. Engl. 1966, 5, 447. (d) Hurd, R. N.; De La Mater, G. Chem. Rev. 1961, 61, 45. (e) see also ref 3 and 8.
6. For reviews on the preparation of thioamides, see: (a) Schaumann, E. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 6; Chapter 2.4, pp 419-434. (b) Bauer, W.; Kühlein, K. In Methoden Org. Chem. 1985, E5, 1218. (c) Walter, W.; Bode, K.-D. Angew. Chem., Int. Ed. Engl. 1966, 5, 447. (d) Hurd, R. N.; De La Mater, G. Chem. Rev. 1961, 61, 45. (e) see also ref 3 and 8.
7. For a review on thionation methods, see: Brillon, D. Sulfur Rep. 1992, 12, 297.
8. (a) Hartke, K.; Gerber, H.-D. J. Prakt. Chem. 1996, 338, 763.
9. (b) Use of ultrasound, see: Raucher, S.; Klein, P. J. Org. Chem. 1981, 46, 3558.
10. 3, see: Scheeren, J. W.; Ooms, P. H. J.; Nivard, R. J. F. Synthesis 1973, 149.
11. 3, see: Brillon, D. Synth. Commun. 1990, 20, 3085.
12. (e) Use of RLi, see: Goel, O. P.; Krolls, U. Synthesis 1987, 162.
13. 2O, see: Curphey, T. J. J. Org. Chem. 2002, 67, 6461.
14. Ogata, M.; Matsumoto, H. Heterocycles 1978, 11, 139.
15. Hirabayashi, T.; Inoue, K.; Yokota, K. J. Organomet. Chem. 1975, 92, 139.
16. (a) Steliou, K.; Mrani, M. J. Am. Chem. Soc. 1982, 104, 3104.
17. (b) Wojtkowski, P. W.; Dolfini, J. E.; Kocy, O.; Cimarusti, C. M. J. Am. Chem. Soc. 1975, 97, 5628.
18. Cava, M. P.; Levinson, M. I. Tetrahedron 1985, 41, 5061.
19. Ley, S. V.; Leach, A. G.; Storer, R. I. J. Chem. Soc., Perkin Trans. 1 2001, 358.
20. Varma, R. S.; Kumar, D. Org. Lett. 1999, 1, 697.
21. Ilankumaran, P.; Ramesha, A. R.; Chandrasekaran, S. Tetrahedron Lett. 1995, 36, 8311.
22. Smith, D. C.; Lee, S. W.; Fuchs, P. L. J. Org. Chem. 1994, 59, 348.
23. Bodine, J. J.; Kaloustian, M. Synth. Commun. 1982, 12, 787.
24. (a) Amidines, see: Charette, A. B.; Grenon, M. Tetrahedron Lett. 2000, 41, 1677.
25. (b) Thiazolines, see: Charette, A. B.; Chua, P. J. Org. Chem. 1998, 63, 908.
26. (c) Esters, see: Charette, A. B.; Chua, P. Synlett 1998, 163.
27. (d) Cyclic Ortho esters, see: Charette, A. B.; Chua, P. Tetrahedron Lett. 1997, 38, 8499.
28. Charette, A. B.; Grenon, M. Can, J. Chem. 2001, 79, 1694.
29. Charette, A. B.; Chua, P. Tetrahedron Lett. 1998, 39, 245.
30. For instance, thioamides 2c (80%), 2d (63%), 2f (94%), and 5b (90%) were obtained after adding NaSH (3.0 equiv) to the activated amides at 0 °C.
31. Kleinberg, J. Inorg. Synth. 1963, 7, 128.
32. (a) Spychala, J. Tetrahedron 2000, 56, 7981.
33. (b) Spychala, J. Synth. Commun. 1997, 27, 3431.
34. This compound has been previously reported, but no spectral characterization was available: Takikawa, Y.; Shimada, K.; Sato, K.; Sato, S.; Takizawa, S. Bull. Chem. Soc. Jpn 1985, 58, 995.
35. Charette, A. B.; Grenon, M.; Lemire, A.; Pourashraf, M.; Martel, J. J. Am. Chem. Soc. 2001, 123, 11829.
36. The reaction was also performed on a 25 mmol scale with amide lg according to method A (84%).