A simple method for the conversion of carboxylic acids into thioacids with Lawesson's reagent

Tetrahedron Letters

Volumn 50, Issue 48, 2009, Pages 6684-6686

  Rao, Yu ^a   Li, Xuechen ^a   Nagorny, Pavel ^a   Hayashida, Joji ^a   Danishefsky, Samuel J ^a,b  

^a MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

^b Howard Hughes Medical Institute   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; HYDROGEN SULFIDE; LAWESSON REAGENT; REAGENT; THIOACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 70349773085     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.09.080     Document Type: Article

References (30)

1. Mapp A.K., and Dervan P.B. Tetrahedron Lett. 41 (2000) 9451-9454
2. Barlett K.N., Kolakowski R.V., Katukojvala S., and Williams L.J. Org. Lett. 8 (2006) 823-826
3. Crich D., Sana K., and Guo S. Org. Lett. 9 (2007) 4423-4426
4. Crich D., and Sharma I. Angew. Chem., Int. Ed. 48 (2009) 2355-2358
5. Crich D., and Sasaki K. Org. Lett. 11 (2009) 3514-3517
6. Merkx R., van Haren M.J., Rijkers D.T.S., and Liskamp R.M.J. J. Org. Chem. 72 (2007) 4574-4577
7. Kolakowski R.V., Shangguan N., Sauers R.R., and Williams L.J. J. Am. Chem. Soc. 128 (2006) 5695-5702
8. Barlett K.N., Kolakowski R.V., Katukojvala S., and Williams L.J. Org. Lett. 8 (2006) 823-826
9. Tam J.P., Lu Y.-A., Liu C.-F., and Shao J. Proc. Natl. Acad. Sci. U.S.A. 92 (1995) 12485-12489
10. Dawson P.E., Muir T.W., Clark-Lewis I., and Kent S.B.H. Science 266 (1994) 776-779
11. Yamashiro D., and Li C.H. Int. J. Pept. Protein Res. 31 (1988) 322-334
12. Blake J., Yamashiro D., Ramasharma K., and Li C.H. Int. J. Pept. Protein Res. 28 (1986) 468-476
13. Blake J., and Li C.H. Proc. Natl. Acad. Sci. U.S.A. 78 (1981) 4055-4058
14. Nagorny P., Fasching B., Li X., Chen G., Aussedat B., and Danishefsky S.J. J. Am. Chem. Soc. 131 (2009) 5792-5799
15. Stockdill J.L., Wu X., and Danishefsky S.J. Tetrahedron Lett. 50 (2009) 5152-5155
16. Wu X., Yuan Y., Li X., and Danishefsky S.J. Tetrahedron Lett. 50 (2009) 4666-4669
17. Yuan Y., Zhu J., Li X., Wu X., and Danishefsky S.J. Tetrahedron Lett. 50 (2009) 2329-2333
18. Rao, Y.; Li, X.; Danishefsky, S. J. J. Am. Chem. Soc. 2009, 131, 12924-12926.
19. Cronyn M.W., and Jiu J. J. Am. Chem. Soc. 74 (1952) 4726
20. Crich D., and Bowers A.A. Org. Lett. 9 (2007) 5323-5325
21. Vetter S. Synth. Commun. 28 (1998) 3219-3223
22. Zhang X., Lu X., and Liu C. Tetrahedron Lett. 49 (2008) 6122-6125
23. Gaertner H., Villain M., Botti P., and Canne L. Tetrahedron Lett. 45 (2004) 2239-2241
24. Ozturk T., Ertas E., and Mert O. Chem. Rev. 107 (2007) 5210-5278
25. Cava M.lP., and Levinson M.I. Tetrahedron 41 (1985) 5061-5087
26. Schmidt A., Merkel L., and Eisfeld W. Eur. J. Org. Chem. 10 (2005) 2124-2130
27. Nishio T. Chem. Commun. 4 (1989) 205-206
28. Varma R.S., and Kumar D. Org. Lett. 1 (1999) 697-700
29. Filippi J.-J., Fernandez X., Lizzani-Cuvelier L., and Loiseau A.-M. Tetrahedron Lett. 44 (2003) 6647-6650
30. When the reaction was carried out under the microwave conditions, extensive decomposition of the starting material, 17, and a low yield of 18 were observed. It is highly possible that the internal amide group may be competing with the carboxylic acid functionality during the course of the reaction with LR under the microwave conditions. However, the corresponding reaction was found to proceed at room temperature, albeit at a slower rate. There is a possibility that the superior reactivity of 17 at room temperature is facilitated by the intermediacy of the oxazolone. Further studies, which will shed some light into the origins of this effect, will be reported in a due course.