A simple and effective method for the thionation of amides to thioamides using Al2O3-supported P4S10

Letters in Organic Chemistry

Volumn 2, Issue 4, 2005, Pages 330-333

  Poupaert, Jacques H ^a   Carato, Pascal ^b   McCurdy, Christopher R ^c  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

^b Faculté des Sciences Pharmaceutiques et Biologiques Université de Lille   (France)

^c UNIVERSITY OF MISSISSIPPI   (United States)

Author keywords

Heterocycles; Lawesson's reagent; Supported reagents; Thioamide; Thionation

Indexed keywords

EID: 46149102965     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/1570178054038957     Document Type: Review

References (32)

1. Block, E. Reactions of Organosulfur Compounds; Academic Press: New York, 1978.
2. Cremlyn, R. J. An Introduction to Organosulfur Chemistry; John Wiley & Sons: New York, 1996.
3. Ach, D.; Reboul, V.; Metzner P. Eur. J. Org. Chem. 2003, 3398-3406.
4. Liebeskind, L. S.; Srogl, J.; Cecile Savarin, C.; Polanco, C. Pure Appl. Chem. 2002, 74, 115.
5. Muccioli, G. G.; Poupaert, J. H.; Wouters, J.; Norberg, B.; Poppitz, W.; Scriba, G. K.; Lambert, D. M. Tetrahedron 2003, 59, 1301.
6. Muccioli, G. G.; Wouters, J.; Poupaert, J. H.; Norberg, B.; Poppitz, W.; Scriba, G. K.; Lambert, D. M. Org Lett. 2003, 5, 3599.
7. Ooms, F.; Wouters, J.; Oscari, O.; Happaerts, T.; Bouchard, G.; Carrupt, P. A.; Testa, B.; Lambert, D. M. J. Med. Chem. 2002, 45, 1748.
8. Padwa, A.; Scott Beall, L.; Heidelbaugh, T. M.; Liu, B.; Sheehan, S. M. J. Org. Chem. 2000, 65, 2684.
9. May, P. J.; Bradley, M.; Harrowven, D. C.; Pallin, D. Tetrahedron Lett. 2000, 41, 1627.
10. Harrowven, D. C.; Lucas, M. C.; Howes, P. D. Tetrahedron Lett. 1999, 40, 4443.
11. Metzner, P. Synthesis 1992, 1185.
12. Katritzky, A. L.; Moutou, J. L.; Yang, Z. Synlett 1995, 99.
13. Murguia, M. C.; Rossi, R. A. Tetrahedron Lett. 1997, 38, 1335.
14. Jang, S.-Y.; Ha Y. H.; Ko S. W.; Lee W.; Lee J.; Kim S.; Kim Y. W.; Ha H.-J. Bioorg. Med. Chem. Lett. 2004, 14, 3881.
15. Schmidt, U.; Luttringhaus, A.; Trefzger, H. Liebigs Ann. Chem. 1960, 631, 129.
16. For a review, see: Brillon, D. Sulfur Rep. 1992, 12, 297.
17. For a review, see: Cava, M. P.; Levinson, M. I. Tetrahedron 1985, 41, 5061.
18. Pedersen, B. S.; Lawesson, S. O. Tetrahedron 1979, 35, 2433.
19. Thomsen, I.; Clausen, K.; Scheibye, S.; Lawesson, S. O. Org. Synth. 1984, 62, 158.
20. Yde, B.; Yousif, N. M.; Pedersen, U.; Thomsen, I.; Lawesson, S. O. Tetrahedron 1984, 40, 2047.
21. Pedersen, B. S.; Scheibye, S.; Clausen, K.; Lawesson, S. O. Bull. Soc. Chim. Belg. 1978, 87, 293.
22. J. Scheibye, S.; Pedersen, B. S.; Lawesson, S. O. Bull. Soc. Chim. Belg. 1978, 87, 229.
23. Curphey, T. J. J. Org. Chem. 2002, 67, 6461.
24. Curphey, T. J. Tetrahedron Lett. 2002, 43, 371.
25. Curphey, T. J. Tetrahedron Lett. 2000, 41, 9963.
26. Pollshettiwar, V.; Kaushik, M. P. Tetrahedron Lett. 2004, 45, 6255.
27. Hino, T.; Tsuneoka, K.; M. Nakagawa, M.; Akaboshi, S. Chem. Pharm. Bull. 1969, 17, 550.
28. Gupta, M.; Pau,l S.; Gupta, R. Synth. Commun. 2001, 31, 63.
29. Cherkasov, R. A.; Kutyrev, G. A.; Pudovik, A. N. Tetrahedron 1985, 41, 2567.
30. Isaacs, N. S.; Ismail, F.; Hilton, M. J.; Coulson, M. J. Phys. Org. Chem. 1998, 11, 1.
31. (30)Poupaert, J. H.; Cavalier, R.; Claesen, M. H.; Dumont, P. A. J. Med. Chem. 1975, 18, 1268.
32. Hussaini, S. R., Moloney, M. G. Tetrahedron Lett. 2004, 45, 1125.