One-Pot Regioselective Synthesis of 4-Bromopyrazole Derivatives Under Solvent Free Conditions
DOI:
https://doi.org/10.29356/jmcs.v55i4.806Keywords:
4-bromopyrazole, solvent free, N-bromosaccharin, 1, 3- diketone, arylhydrazine.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.
Downloads
References
(a) Gioiello, A.; Khamidullina, A.; Fulco, M. C.; Venturoni, F.; Zlotsky, S.; Pellicciari, R. Tetrahedron Lett. 2009, 50, 5978-5980. (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. Agric. FoodChem. 2008, 56, 10160–10167.
Li, G.; Kakarla, R.; Gerritz, S. W. Tetrahedron Lett. 2007, 48, 4595-5499.
Salaheldin, A. M.; Oliveira-Campos, A. M. F.; Rodrigues, L. M. Tetrahedron Lett. 2007, 48, 8819-8822.
(a) Wang, X. J.; Tan, J.; Grozinger, K. Tetrahedron Lett. 2000, 41, 4713-4716 (b) Itoh, N.; Izumi. Y.; Yamada, H. Biochemistry 1987, 26, 282–289. (c) Foti, F.; Grassi, G.; Risitano, F. Tetrahedron Lett. 1999, 40, 2605-2606.
Stefani, H. A.; Pereira, C. M. P.; Almeida, R. B.; Braga, R. C.; Guzen, K. P.; Cella, R. Tetrahedron Lett. 2005, 46, 6833-6837. (b) Day, R. A.; Blake, J. A.; Stephens, C. E. Synthesis 2003, 10, 1586-1590.
Jeon, S. L.; Choi, J. H.; Kim, B. T.; Jeong, I. H. J. Fluorine Chem. 2007, 128, 1191-1197.
Wang, Z. X.; Qin, H.L. Green Chem. 2004, 6, 90-92.
Chen, X.; She, J.; Shang, Z. C.; Wu, J.; Zhang, P. Synth. Commun 2009, 39, 947-957.
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.
Polshettiwar, V.; Varma, R. S. Tetrahedron Lett. 2008, 49, 397- 400.
Bouabdallah, I.; Touzani, R.; Zidane, I.; Ramdani, A.; Radi, S. Arkivoc part (xii). 2006, 138-144.
(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. (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.
Schlosser. M.; Angew. Chem. Int. Ed. 2006, 45, 5432–5446.
Havanur, S.; Badami, B.V.; Puranik, G.S. Can .J. Chem. 1983, 61,154-155.
Firouzabadi, H.; Iranpoor, N.; Ebrahimzadeh. F. Tetrahedron Lett. 2006, 47, 1771-1775.
Ballini, R.; Palmieri A.; Righi, P. Tetrahedron 2007, 63, 12099-12121.
Alinezhad, H.; Tajbakhsh, M.; Zare M. Synth. Commun. 2009, 39, 2907-2916.
Touzot, A.; Soufyane, M.; Berber, H.; Toupet, L.; Mirand, C. J. Fluorine Chem. 2004, 125, 1299-1304.
Song, L. P.; Zhu, S. Z. J. Fluorine Chem. 2001, 111, 201-205.
Lakouraj, M. M.; Akbari, A. Indian. J. Chem, B. 2003, 1165- 1167.
Souza, S. P. L.; Silva, J. F. M.; Mattos, M. C. S. Synth. Commun. 2003, 33, 935-939.
Downloads
Published
Issue
Section
License
Authors who publish with this journal agree to the following terms:
- Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.
- Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal.