N-Bromosuccinimide assisted oxidation of 5-aminopyrazoles: formation of bis diazenylderivatives

Tetrahedron Letters

Volumn 48, Issue 50, 2007, Pages 8819-8822

  Salaheldin, Abdellatif M ^a   Oliveira Campos, Ana M F ^a   Rodrigues, Lígia M ^a  

^a UNIVERSITY OF MINHO   (Portugal)

Author keywords

Azo dyes; Bromination; Dimers; NBS; Pyrazole

Indexed keywords

5 AMINOPYRAZOLE DERIVATIVE; ACETIC ACID; AZO DYE; BIS DIAZENYL DERIVATIVE; BROMINE; DIAZENE DERIVATIVE; HETEROCYCLIC COMPOUND; N BROMOSUCCINIMIDE; PYRAZOLE; UNCLASSIFIED DRUG; WATER; ZINC DERIVATIVE;

ARTICLE; BROMINATION; DIMERIZATION; OXIDATION KINETICS; PRODUCT RECOVERY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REDUCTION KINETICS; SYNTHESIS;

EID: 36048990067     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.10.079     Document Type: Article

References (35)

1. Elguero J., Goya P., Jagerovic N., and Silva A.M.S. Targets in Heterocyclic System Vol. 6 (2002), Italian Society of Chemistry, Roma 167-203
2. Wustrow D.J., Capiris T., Rubin R., Knobelsdorf J.A., Akunne H., Davis M.D., MacKenzie R., Pugsley T.A., Zoski K.T., Heffner T.G., and Wise L.D. Bioorg. Med. Chem. Lett. 8 (1998) 2067
3. Penning T.D., Talley J.J., Bertenshaw S.R., Carter J.S., Collins P.W., Docter S., Graneto M.J., Lee L.F., Malecha J.W., Miyashiro J.M., Rogers R.S., Rogier D.J., Yu S.S., Anderson G.D., Burton E.G., Cogburn J.N., Gregory S.A., Koboldt C.M., Perkins W.E., Seibert K., Veenhuizen A.W., Zhang Y.Y., and Isakson P.C. J. Med. Chem. 40 (1997) 1347
4. Li Y., Zhang H.-Q., Liu J., Yang X.-P., and Liu Z.-J. J. Agric. Food Chem. 54 (2006) 3636
5. Siddall T.L., Ouse D.G., Benko Z.L., Garvin G.M., Jackson J.L., McQuiston J.M., Ricks M.J., Thibault T.D., Turner J.A., VanHeertum J.C., and Weimer M.R. Pest Manage. Sci. 58 (2002) 1175
6. Soliman R., and Darwish S.A.S. J. Med. Chem. 26 (1983) 1659
7. Dressen D., Garofalo A.W., Hawkinson J., Hom D., Jagodzinski J., Marugg J.L., Neitzel M.L., Pleiss M.A., Szoke B., Tung J.S., Wone D.W.G., Wu J., and Zhang H. J. Med. Chem. (2007). ASAP Article doi:10.1021/jm051292n
8. Surendra K., Krishnaveni N.S., Kumar V.P., Sridhar R., and Rao K.R. Tetrahedron Lett. 46 (2005) 4581
9. Karimi B., Hazarkhani H., and Maleki J. Synthesis (2005) 279
10. Talluri S.K., and Sudalai A. Org. Lett. 7 (2005) 855
11. Podgorsek A., Stavber S., Zupan M., and Iskra J. Tetrahedron Lett. 47 (2006) 1097
12. Pravst I., Zupan M., and Stavbre S. Tetrahedron Lett. 47 (2006) 4707
13. Wu J., Sun W., Sun X., and Xia H.-G. Green Chem. 8 (2006) 365
14. Gonçalves S.M.T., Oliveira-Campos A.M.F., Rodrigues L.M., Proença F.R.P., Griffiths J., Maia H.L.S., Martin K., and Hrdina R. J. Chem. Res. (2004) 115
15. Gupta S., Sivasubramanian A., Rodrigues L.M., Esteves A.P., Hrdina R., and Oliveira-Campos A.M.F. Dyes Pigments 75 (2007) 82
16. Gupta, S.; Rodrigues, L. M.; Esteves, A. P.; Oliveira-Campos, A. M. F.; M. Nascimento, S. J.; Nazareth, N.; Cidade, H.; Neves, M. P.; Pinto, E. F. M.; Cerqueira, N. M. F. and Brás, N. Eur. J. Med. Chem., in press, doi:10.1016/j.ejmech.2007.06.002.
17. Day R.A., Blake J.A., and Stephens C.E. Synthesis 10 (2003) 1586
18. Stefani H.A., Pereira C.M.P., Almeida R.B., Braga R.C., Guzen K.P., and Cella R. Tetrahedron Lett. 46 (2005) 6833
19. Foti F., Grassi G., and Risitano R. Tetrahedron Lett. 40 (1999) 2605
20. Li G., Kakarla R., and Gerritz S.W. Tetrahedron Lett. 48 (2007) 4595
21. Jeon, S. L.; Choi, J. H.; Kim, B. T.; and Jeong, I. H. Journal of Fluorine Chemistry, in press, doi:10.1016/j.jfluchem.2007.04.029.
22. Mitchell R.H., Lai Y.-H., and Williams R.V. J. Org. Chem. 44 (1979) 4733
23. Carreño M.C., Garćia Ruano J.L., Sanz G., Toledo M.A., and Urbano A. J. Org. Chem. 60 (1995) 5228
24. Meana A., Rodríguez J.F., Sanz-Tezdedor M.A., and Garćia Ruano J.L. Synlett (2003) 1678
25. Auerbach J., Weissmann S.A., Blacklock T.J., Angeles M.R., and Hoogstein K. Tetrahedron Lett. 34 (1993) 931
26. Oberhauser T. J. Org. Chem. 62 (1997) 4504
27. Diwu Z.J., and Lown J.W. Tetrahedron 48 (1992) 45
28. Eguchi H., Kawaguchi H., Yoshinaga S., Nishida A., Nishiguchi T., and Fujisaki S. Bull. Chem. Soc. Jpn. 67 (1994) 1918
29. Fujisaki S., Eguchi H., Omura A., Okamoto A., and Nishida A. Bull. Chem. Soc. Jpn. 66 (1993) 1576
30. Kuo C.-W., Shivaji V., and Yao C.-F. Tetrahedron Lett. 47 (2006) 8523
31. Joshaghani M., Rafiee E., Shahbazi F., Jafari H., Amiri S., and Omidi M. Arkivoc (2007) 164
32. Lim Y.-K., Lee K.-S., and Cho C.-G. Org. Lett. 5 (2003) 979
33. Talluri S.K., and Sudalai A. Org. Lett. 7 (2005) 855
34. Stefani H.A., Pereira C.M.P., Almeida R.B., Braga R.C., Guzen K.P., and Cella R. Tetrahedron Lett. 46 (2005) 6833
35. 4: C, 47.68; H, 3.27; N, 20.22. Found: C, 47.68; H, 3.37; N, 19.96.