SciELO - Scientific Electronic Library Online

 
vol.55 issue4Preparation and Characterization of Hybrid Materials of Epoxy Resin Type Bisphenol A With Silicon and Titanium Oxides by Sol Gel ProcessBio-ethanol Obtained by Fermentation Process with Continuous Feeding of Yeast author indexsubject indexsearch form
Home Pagealphabetic serial listing  

Services on Demand

Journal

Article

Indicators

Related links

  • Have no similar articlesSimilars in SciELO

Share


Journal of the Mexican Chemical Society

Print version ISSN 1870-249X

J. Mex. Chem. Soc vol.55 n.4 Ciudad de México Oct./Dec. 2011

 

Article

 

One–Pot Regioselective Synthesis of 4–Bromopyrazole Derivatives Under Solvent Free Conditions

 

Heshmatollah Alinezhad,* Mahmood Tajbakhsh, and Mahboobeh Zare

 

Faculty of Chemistry, Mazandaran University, Babolsar, Iran. heshmat@umz.ac.ir.

 

Received June 2, 2011.
Accepted September 2, 2011.

 

Abstract

An efficient protocol for the one pot regioselective synthesis of 4–bromopyrazole derivatives from 1,3–diketones, arylhydrazines and N–bromosaccharin, in the presence of silica gel supported sulfuric acid as heterogeneous catalyst, under solvent free conditions, is reported.

Key words: 4–bromopyrazole, solvent free, N–bromosaccharin, 1,3–diketone, arylhydrazine.

 

Resumen

En este trabajo se informa de un método nuevo y eficiente para la síntesis regioselectiva y en una sola etapa de derivados del 4–bromopirazol, a partir de 1,3– dicetonas, arilhidracinas y N–bromo–sacarina empleando como catalizador ácido sulfúrico soportado en gel de sílice, en ausencia de disolvente.

Palabras clave: 4–bromopirazol, libre de solventes, N–bromosacarina, 1,3–dicetona, arilhidracina.

 

DESCARGAR ARTÍCULO EN FORMATO PDF

 

References

1. (a) Gioiello, A.; Khamidullina, A.; Fulco, M. C; Venturoni, F.; Zlotsky, S.; Pellicciari, R. Tetrahedron Lett. 2009, 50, 5978–5980.         [ Links ] (b) Ouyang, G.; Cai, X. J; Chen, Z.; Song, B. A.; Bhadury, P. S.; Yang, S.; Jin, L. H; Xue, W.; Hu, D.Y.; Zeng, S. J. Agrie. Food Chem. 2008, 56, 10160–10167.         [ Links ]

2. Li, G.; Kakarla, R.; Gerritz, S. W. Tetrahedron Lett. 2007, 48, 4595–5499.         [ Links ]

3. Salaheldin, A. M.; Oliveira–Campos, A. M. F.; Rodrigues, L. M. Tetrahedron Lett. 2007, 48, 8819–8822.         [ Links ]

4. (a) Wang, X. J.; Tan, J.; Grozinger, K. Tetrahedron Lett. 2000, 41, 4713–4716 (b) Itoh,         [ Links ] N.; Izumi. Y.; Yamada, H. Biochemistry 1987, 26,282–289.         [ Links ] (c) Foti, F.; Grassi, G.; Risitano, F. Tetrahedron Lett. 1999, 40, 2605–2606.         [ Links ]

5. Stefani, H. A.; Pereira, C. M. P.; Almeida, R. B.; Braga, R. C; Guzen, K. P.; Celia, R. Tetrahedron Lett. 2005, 46, 6833–6837.         [ Links ] (b) Day, R. A.; Blake, J. A.; Stephens, C. E. Synthesis 2003, 10, 1586–1590.         [ Links ]

6. Jeon, S. L.; Choi, J. H.; Kim, B. T.; Jeong, I. H. J. Fluorine Chem. 2007,128, 1191–1197.         [ Links ]

7. Wang, Z. X.; Qin, H.L. Green Chem. 2004, 6, 90–92.         [ Links ]

8. Chen, X.; She, J.; Shang, Z. C; Wu, J.; Zhang, P. Synth. Commun 2009, 39, 947–957.         [ Links ]

9. Fustero, S.; Roman, R.; Sanz–Cervera, J. F.; Simon–Fuentes, A.; Cunat, A. C; Villanova, S.; Murguia M. J. Org. Chem. 2008, 73, 3523–3529.         [ Links ]

10. Polshettiwar, V.; Varma, R. S. Tetrahedron Lett. 2008, 49, 397–400.         [ Links ]

11. Bouabdallah, I.; Touzani, R.; Zidane, I; Ramdani, A.; Radi, S. Arkivoc part (xii). 2006, 138–144.         [ Links ]

12. (a) Martins, M. A. P.; Scapin, E.; Frizzo, C. P.; Rosa, F. A.; Bonacorso, H. G.; Zanatta, N. J. Braz. Chem. Soc. 2009, 20, 205–213.         [ Links ] (b) Dwyer, M. P.; Paruch, K.; Alvarez, C; Doll, R. J.; Keertikar, K.; Duca, J.; Fischmann, T. O.; Hruza, A.; Madison, V.; Lees, E.; Parry, D.; Seghezzi, W.; Sgambellone, N.; Shanahan, F.; Wiswell, D.; Guzi T. J. Bioorg. Med. Chem. Lett. 2007,17, 6216–6219.         [ Links ]

13. Schlosser. M.; Angew. Chem. Int. Ed. 2006, 45, 5432–5446.         [ Links ]

14. Havanur, S.; Badami, B.V.; Puranik, G.S. Can J. Chem. 1983, 61, 154–155.         [ Links ]

15. Firouzabadi, H; Iranpoor, N.; Ebrahimzadeh. F. Tetrahedron Lett. 2006, 47, 1771–1775.         [ Links ]

16. Ballini, R.; Palmieri A.; Righi, P. Tetrahedron 2007, 63, 12099–12121.         [ Links ]

17. Alinezhad, H; Tajbakhsh, M.; Zare M. Synth. Commun. 2009, 39, 2907–2916.         [ Links ]

18. Touzot, A.; Soufyane, M.; Berber, H; Toupet, L.; Mirand, C. J. Fluorine Chem. 2004, 125, 1299–1304.         [ Links ]

19. Song, L. P.; Zhu, S. Z. J. Fluorine Chem. 2001, 111, 201–205.         [ Links ]

20. Lakouraj, M. M.; Akbari, A. Indian. J. Chem, B. 2003, 1165–1167.         [ Links ]

21. Souza, S. P. L.; Silva, J. F. M.; Mattos, M. C. S. Synth. Commun. 2003, 33, 935–939.         [ Links ]

Creative Commons License All the contents of this journal, except where otherwise noted, is licensed under a Creative Commons Attribution License