An efficient method for the synthesis of disubstituted thioureas via the reaction of N,N′-di-Boc-substituted thiourea with alkyl and aryl amines under mild conditions

Tetrahedron Letters

Volumn 49, Issue 22, 2008, Pages 3687-3690

  Yin, Biaolin ^a   Liu, Zhaogui ^a   Yi, Mingjun ^a   Zhang, Jiancun ^a  

^a GUANGZHOU INSTITUTES OF BIOMEDICINE AND HEALTH   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC AMINE; AROMATIC AMINE; THIOUREA DERIVATIVE; TRIFLUOROACETIC ANHYDRIDE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE;

EID: 43049124744     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.03.158     Document Type: Article

References (36)

1. Lee J., Lee J., Kang M., Shin M., Kim J.-M., Kang S.-U., Choi H.-K., Suh Y.-G., Park H.-G., Oh U., Kim H.-D., Park Y.-H., Ha H.-J., Kim Y.-H., Toth A., Wang Y., Tran R., Pearce L.V., Lundberg D.J., and Blumberg P.M.. J. Med. Chem. 46 (2003) 3116
2. Ranise A., Spallarossa A., Bruno O., Schenone S., Fossa P., Menozzi G., Bondavalli F., Mosti L., Capuano A., Mazzeo F., Falcone G., and Filippelli W. Il Farmaco 58 (2003) 765
3. Silvio C., Fernando C., Macedo J., Giselle A.N., Costa M.T., Rodrigues J., Rosival B.V., Verde L.C., Souza N., Ivo V., Carlito L., and Sá Fernando P. Monatsh. Chem. 138 (2007) 511
4. Omar A.-Mohsen.M.E., Farghaly A.M., Hazzai A.A.B., Eshba N.H., Sharabi F.M., and Daabees F.M. J. Pharm. Sci. 70 (2006) 1075
5. Krishnamurthy R., Govindaraghavan S., and Narayanasamy J. Pestic. Sci. 52 (1999) 145
6. Kearney P.C., Frenandez M., and Flygare J.A. J. Org. Chem. 63 (1998) 196
7. Patil D.G., and Chedekel M.R. J. Org. Chem. 49 (1984) 997
8. Kasmi S., Hamelin J., and Benhaoua H. Tetrahedron Lett. 39 (1998) 8093
9. Kidwai M., Venkataramanan R., and Dave B. Green Chem. 3 (2001) 278
10. Paul S., Gupta M., Gupta R., and Loupy A. Synthesis (2002) 75
11. Anshu D., Kapil A., and Meha S. Synth. Commun. 34 (2004) 1141
12. Heinelt U., Schultheis D., Jager S., Iindenmaire M., Pollex A., and Beckmann H.S.G. Tetrahedron 60 (2004) 9883
13. Love B., Bender P.E., Bowman H., Helt A., Mclean R., and Jen T. J. Med. Chem. 15 (1972) 1024
14. Frank R.L., and Smith P.V. Org. Synth. Coll. Vol. III (1955) 735
15. Rasmussen C.R., Villani Jr. F.J., Weaner L.E., Reynolds B.E., Hood A.R., Hecker L.R., Nortey S.O., Hanslin A., Costanzo M.J., Powell E.T., and Molinari A.J. Synthesis (1988) 456
16. Moor M.L., and Crossely F.S. Org. Synth. Coll. Vol. III (1955) 617
17. Bernstein J., Yale H.L., Losee K., Holsing M., Martins J., and Lott W.A. J. Am. Chem. Soc. 73 (1951) 906
18. Erickson J.G. J. Org. Chem. 21 (1956) 483
19. Vázquez J., Bemès S., Reyes Y., Moya M., Sharma P., Alvarez C., and Gutiérrez R. Synthesis (2004) 1955
20. Katritzky A.R., Kirichenko N., Rogovoy B.V., Kister J., and Tao H. Synthesis (2004) 1799
21. Ciszewski L., Xu D., Repic O., and Blacklock T.J. Tetrahedron Lett. 45 (2004) 8091
22. Mitsuo K., Masato S., Keiko T., and Tadashi A. Tetrahedron Lett. 46 (2005) 5841
23. Falmagne J.B., Escudero J., Taleb-saharaoui S., and Ghosez L. Angew. Chem., Int. Ed. Engl. 20 (1981) 879
24. Sisti N.J., Fowler F.W., and Grierson D.S. Synlett (1991) 816
25. Thomas E.W. Synthesis (1993) 767
26. Barbaro G., Battaglia A., Bruno C., Giorgianni P., and Guerrini A. J. Org. Chem. 61 (1996) 8480
27. Sisti N.J., Zeller E., Grierson D.S., and Fowler F.W. J. Org. Chem. 62 (1997) 2093
28. Charette A.B., and Chua P. J. Org. Chem. 63 (1998) 908
29. Charette A.B., and Chua P. Tetrahedron Lett. 38 (1997) 8499
30. Charette A.B., and Chua P. J. Org. Chem. 63 (1998) 908
31. Charette A.B., and Chua P. Synlett (1998) 163
32. Charette A.B., and Chua P. Tetrahedron Lett. 39 (1998) 245
33. Charette A.B., and Grenon M. Tetrahedron Lett. 41 (2000) 1677
34. Exposito A., Femandez-Suarez M., Iglesias T., Munoz L., and Riguera R. J. Org. Chem. 66 (2001) 4206
35. 2S: C, 58.62; H, 6.81; N, 10.52; S, 12.04. Found: C, 58.44; H, 6.86; N, 10.64; S, 12.33.
36. 7S: C, 51.45; H, 6.59; N, 9.47; S, 7.23. Found: C, 51.67; H, 6.33; N,9.50; S, 7.10.