Pronounced ionic liquid effect in the synthesis of biologically active isatin-3-oxime derivatives under acid catalysis

Tetrahedron Letters

Volumn 49, Issue 39, 2008, Pages 5639-5641

  Pinto, Angelo C ^a   Lapis, Alexandre A Moreira ^b,d   da Silva, Barbara Vasconcellos ^a   Bastos, Renato S ^a   Dupont, Jaïrton ^b   Neto, Brenno A D ^c  

^a FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

^b FEDERAL UNIVERSITY OF RIO GRANDE DO SUL   (Brazil)

^c PONTIFICAL CATHOLIC UNIVERSITY OF RIO GRANDE DO SUL   (Brazil)

^d UNIVERSIDADE FEDERAL DO PAMPA   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

BRONSTED ACID; IMIDAZOLE DERIVATIVE; IONIC LIQUID; LEWIS ACID; OXIME DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; SYNTHESIS;

EID: 49349104098     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.07.067     Document Type: Article

References (34)

1. Zhou L., Liu Y., Zhang W., Wei P., Huang C., Pei J., Yuan Y., and Lai L. J. Med. Chem. 49 (2006) 3440
2. Matheus M.E., Violante F.A., Garden S.J., Pinto A.C., and Fernandes P.D. Eur. J. Pharmacol. 556 (2007) 200
3. Yogeeswari P., Sriram D., Thirumurugan R., Raghavendran J.V., Sudhan K., Pavana R.K., and Stables J. J. Med. Chem. 48 (2005) 6202
4. Ine K.L., Locke J.M., Ranson M., Pyne S.G., and Bremner J.B. J. Med. Chem. 50 (2007) 5109-5117
5. Da Silva J.M., Garden S.J., and Pinto A.C. J. Braz. Chem. Soc. 12 (2001) 273 and references cited therein
6. Grougnet R., Magiatis P., Fokialakis N., Mitaku S., Skaltsounis A.-L., Tillequin F., Sévenet T., and Litaudon M. J. Nat. Prod. 68 (2005) 1083
7. Jensen, B. S.; Jorgensen, T. D.; Ahring, P. K.; Christophersen, P.; Strobaek, D.; Teuber, L.; Olesen, S. P. WO 00/69794, November 23, 2000.
8. Sandmeyer T. Helv. Chim. Acta 2 (1919) 234
9. Marvel C.S., and Hiers G.S. Org. Synth. 1 (1941) 327
10. Rewcastle G.W., Sutherland H.S., Weir C.A., Blackburn A.G., and Denny W.A. Tetrahedron Lett. 46 (2005) 8719
11. Prinz W., Kaile A., and Levy P.R. J. Chem. Res. (S) (1978) 116
12. Prinz W., Kaile A., and Levy P.R. J. Chem. Res. (M) (1978) 1347
13. Pasto D.J., and Johnson C.R. In: Cliffs N.I. (Ed). Organic Structure Determination (1969), Prentice-Hall, Englewood 391
14. Kearney T., Harris P.A., Jackson A., and Joule J.A. Synthesis (1992) 769
15. Dupont J., de Souza R.F., and Suarez P.A.Z. Chem. Rev. 102 (2002) 3667
16. See for example:. Chauvin Y., Mussmann L., and Olivier H. Angew. Chem., Int. Ed. 34 (1996) 2698
17. Carmichael A.J., Earle M.J., Holbrey J.D., McCormac P.B., and Seddon K.R. Org. Lett. 1 (1999) 997
18. de Bellefon C., Pollet E., and Grenouillet P. J. Mol. Catal. A: Chem. 145 (1999) 121
19. Santos L.S., Neto B.A.D., Consorti C.S., Pavam C.H., Almeida W.P., Coelho F., Dupont J., and Eberlin M.N. J. Phys. Org. Chem. 19 (2006) 731
20. For a good review on the acid behavior in ILs see:. Johnson K.E., Pagni R.M., and Bartmess J. Monatsh. Chem. 138 (2007) 1077
21. For other examples see:. Brausch N., Metlen A., and Wasserscheid P. Chem. Commun. (2004) 1552
22. Chauvin Y., Hirschauer A., and Olivier H. J. Mol. Catal. 92 (1994) 155
23. Fei Z.F., Zhao D.B., Geldbach T.J., Scopelliti R., and Dyson P.J. Chem. Eur. J. 10 (2004) 4886
24. Thornazeau C., Olivier-Bourbigou H., Magna L., Luts S., and Gilbert B. J. Am. Chem. Soc. 125 (2003) 5264
25. Pilli R.A., Robello L.G., Camilo N.S., Dupont J., Lapis A.A.M., and Neto B.A.D. Tetrahedron Lett. 47 (2006) 1669
26. Russowsky D., and Neto B.A.D. Tetrahedron Lett. 45 (2004) 1437
27. Russowsky D., and Neto B.A.D. Tetrahedron Lett. 44 (2003) 2923
28. Neto B.A.D., Lapis A.A.M., Mancilha F.S., Vasconcelos I.B., Thum C., Basso L.A., Santos D.S., and Dupont J. Org. Lett. 9 (2007) 4001
29. Lapis A.A.M., Neto B.A.D., Scholten J.D., Nachtigall F.M., Eberlin M.N., and Dupont J. Tetrahedron Lett. 47 (2006) 6775
30. Neto B.A.D., Eberling G., Gonçalves R.S., Gozzo F.C., Eberlin M.N., and Dupont J. Synthesis (2004) 1155
31. Gaillard C., Billard I., Chaumont A., Mekki S., Ouadi A., Denecke M.A., Moutiers G., and Wipff G. Inorg. Chem. 44 (2005) 8355
32. Dupont J. J. Braz. Chem. Soc. 15 (2004) 341
33. Neto B.A.D., Santos L.S., Nachtigall F.M., Eberlin M.N., and Dupont J. Angew. Chem., Int. Ed. 45 (2006) 7251
34. 2O). Overall yields were determined by a combination of isolated products.