Simplified approach to the regiospecific synthesis of trichloromethylpyrazolines using microwave irradiation

Synthetic Communications

Volumn 38, Issue 20, 2008, Pages 3465-3476

  Martins, Marcos A P ^a   Muraro, Paulo ^a   Beck, Paulo ^a   Machado, Pablo ^a   Frizzo, Clarissa P ^a   Zanatta, Nilo ^a   Bonacorso, Helio G ^a  

^a FEDERAL UNIVERSITY OF SANTA MARIA   (Brazil)

Author keywords

Biological activity; Enones; Microwave irradiation; Pyrazoles; Trichloromethyl compounds

Indexed keywords

1 CARBOXAMIDE 5 TRICHLOROMETHYL 3 (4 BROMOPHENYL) 5 HYDROXY 4,5 DIHYDRO 1H PYRAZOLE; 1 CARBOXAMIDE 5 TRICHLOROMETHYL 3 (4 CHLOROPHENYL) 5 HYDROXY 4,5 DIHYDRO 1H PYRAZOLE; 1 CARBOXAMIDE 5 TRICHLOROMETHYL 3 (4 FLUOROPHENYL) 5 HYDROXY 4,5 DIHYDRO 1H PYRAZOLE; 1 CARBOXAMIDE 5 TRICHLOROMETHYL 3 ETHYL 5 HYDROXY 4,5 DIHYDRO 1H PYRAZOLE; 1 CARBOXAMIDE 5 TRICHLOROMETHYL 3 METHYL 5 HYDROXY 4,5 DIHYDRO 1H PYRAZOLE; 1 CARBOXAMIDE 5 TRICHLOROMETHYL 5 HYDROXY 3 (1 METHYLETHYL) 4,5 DIHYDRO 1H PYRAZOLE; 1 CARBOXAMIDE 5 TRICHLOROMETHYL 5 HYDROXY 3 (1,1 DIMETHYLETHYL) 4,5 DIHYDRO 1H PYRAZOLE; 1 CARBOXAMIDE 5 TRICHLOROMETHYL 5 HYDROXY 3 (2 METHYLPROPYL) 4,5 DIHYDRO 1H PYRAZOLE; 1 CARBOXAMIDE 5 TRICHLOROMETHYL 5 HYDROXY 3 (4 NITROPHENYL) 4,5 DIHYDRO 1H PYRAZOLE; 1 CARBOXAMIDE 5 TRICHLOROMETHYL 5 HYDROXY 3 PHENYL 4,5 DIHYDRO 1H PYRAZOLE; 1 CARBOXAMIDE 5 TRICHLOROMETHYL 5 HYDROXY 3 PROPYL 4,5 DIHYDRO 1H PYRAZOLE; 1 CARBOXAMIDE 5 TRICHLOROMETHYL 5 HYDROXY 4,5 DIHYDRO 1H PYRAZOLE; CARBAZIC ACID DERIVATIVE; METHANOL; PYRAZOLINE DERIVATIVE; PYRIDINE; SOLVENT; UNCLASSIFIED DRUG; WATER;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ENVIRONMENT; DRUG STRUCTURE; DRUG SYNTHESIS; MASS SPECTROMETRY; MICROWAVE IRRADIATION; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION TIME;

EID: 53149125714     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802162926     Document Type: Article

References (36)

1. Silva, V. L. M.; Silva, A. M. S.; Pinto, D. C. G. A.; Jagerovic, N.; Callado, L. F.; Cavaleiro, J. A. S.; Elguero, J. Synthesis and pharmacological evaluation of chlorinated N-alkyl-3- and -5-(2-hydroxyphenyl)pyrazoles as CB1 cannabinoid ligands. Montasch. Chem. 2007, 138, 797.
2. Daidone, G.; Maggio, B.; Plescia, S.; Raffa, D.; Musiu, C.; Milia, C.; Perra, G.; Marongiu, M. E. Antimicrobial and antineoplastic activities of new 4-diazopyrazole derivatives. Eur. J. Med. Chem. 1998, 33, 375.
3. Almansa, C.; Gomez, L. A.; Cavalcanti, F. L.; de Arriba, A. F.; Garcia-Rafanell, J.; Form, J. Synthesis and structure-activity relationship of a new series of potent AT1 selective angiotensin II receptor antagonists: 5-(Biphenyl-4-methyl)pyrazoles. J. Med. Chem. 1997, 40, 547.
4. Zhihua, S.; Guan, J.; Michael, F. P.; Kathy, M.; Michael, W. P.; William, M. V.; Monica, S.; Michael, S.; Dave, R. M.; Dennis, C. 1,3- Diarylcycloalkanopyrazoles and diphenyl hydrazides as selective inhibitors of cyclooxygenase-2. Bioorg. Med. Chem. Lett. 2000, 10, 601.
5. Finn, J.; Mattia, K.; Morytko, M.; Ram, S.; Yang, Y.; Wu, X.; Mak, E.; Gallant, P.; Keith, D. Discovery of a potent and selective series of pyrazole bacterial methionyl-tRNA synthetase inhibitors. Bioorg. Med. Chem. Lett. 2003, 13, 2231.
6. Lautens, M.; Roy, A. synthetic studies of the formation of oxazoles and isoxazoles from N-acetoacetyl derivatives: Scope and limitations. Org. Lett. 2002, 555.
7. (a) Padwa, A. 1,3-dipolar cycloaddition chemistry; John Wiley & Sons: New York, 1984; vol. 1;
8. 1: Regioselective synthesis of (ω-Aminoalkyl)pyrazoles from semicyclic 3-chloro-2-propeniminium salts and hydrazines. Synthesis. 1991, 1153;
9. (c) Wang, X.; Tan, J.; Grozinger, K.; Cross-coupling of 1-aryl-5-bromopyrazoles: Regioselective synthesis of 3,5-disubstituted 1-arylpyrazoles. Tetrahedron Lett. 2000, 41, 4713;
10. (d) Katritzky, A. R.; Wang, M.; Zhang, S.; Voronkov, M. V. Regioselective synthesis of polysubstituted pyrazoles and isoxazoles. J. Org. Chem. 2001, 66, 6787.
11. (a) Haddad, N.; Baron, J. Novel application of the palladium-catalyzed N-arylation of hydrazones to a versatile new synthesis of pyrazoles. Tetrahedron Lett. 2002, 43, 2171;
12. (b) Aggarwal, V. K.; de Vicente, J.; Bonnert, R. V. A novel one-pot method for the preparation of pyrazoles by 1,3-dipolar cycloadditions of diazo compounds generated in situ. J. Org. Chem. 2003, 68, 5381;
13. (c) Huang, Y. R.; Katzenellenbogen, J. A. Regioselective synthesis of 1,3,5-triaryl-4-alkylpyrazoles: Novel ligands for the estrogen receptor. Org. Lett. 2000, 2, 2833;
14. (d) Lee, K. Y.; Kim, J. M.; Kim, J. N. Regioselective synthesis of 1,3,4,5-tetrasubstituted pyrazoles from Baylis-Hillman adducts. Tetrahedron Lett. 2003, 44, 6737.
15. Martins, M. A. P.; Cunico, W.; Pereira, C. M. P.; Flores, A. F. C.; Bonacorso, H. G.; Zanatta, N. 4-Alcoxi-1,1,1-trichoro-3-alken-2-ones: Preparation and applications in heterocyclic synthesis. Curr. Org. Synthesis. 2004, 1, 391.
16. Martins, M. A. P.; Emmerich, D. J.; Pereira, C. M. P.; Cunico, W.; Rossato, M.; Zanatta, N.; Bonacorso, H. G. Synthesis of new halo-containing acetylenes and their application to the synthesis of azoles. Tetrahedron Lett. 2004, 45, 4935.
17. (a) Hojo, M.; Masuda, R.; Kokuryo, Y.; Shioda, H.; Matsuo, S. Electrophilic substitutions of olefinic hydrogens, II: Acylation of vinyl ethers and n-vinyl amides. Chem. Lett. 1976, 499;
18. (b) Spiegler, W. Götz, N. Fine einfache Synthese von Isoxazol-5-carbonsaüre. Synthesis 1986, 1, 69;
19. (c) Titze, L. -F.; Meier, H.; Voss, E. Highly efficient syntheses of alkyl 3,3-diakoxypropanoates, alkyl 4-etoxy-2-oxo-3-butenoates, and monoprotected malonaldeydes. Synthesis 1988, 4, 274.
20. Martins, M. A. P.; Pereira, C. M. P.; Cunico, W.; Moura, S.; Rosa, F. A.; Peres, R. L.; Machado, P.; Zanatta, N.; Bonacorso, H. G. Ultrasound promoted synthesis of 5-hydroxy-5-trihalomethyl-4,5-dihydroisoxazoles and β-enamino trihalomethyl ketones in water Ultrason. Sonochem. 2006, 13, 364.
21. Colla, A., Clar, G.; Martins, M. A. P.; Krimmer, S.; Fischer, P. Trihaloacetylated enol ethers General synthetic procedure and heterocyclic ring closure reactions with hydroxylamine. Synthesis. 1991, 483.
22. Nenajdenko, V. G.; Sanin, A. V.; Balenkova, E. S. Preparation of α,β-unsaturated ketones bearing a trifluoromethyl group and their application in organic synthesis. Molecules. 1997, 2, 186.
23. Bonacorso, H. G.; Wastowski, A. D.; Zanatta, N.; Martins, M. A. P. A convenient method to obtain 4,5-dihydro-1H-methylpyrazoles by a ring transformation reaction. Synth. Commun. 2000, 30, 1457.
24. (a) 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.; Isakson, P. C. Synthesis and biological evaluation of the 1,5-diarylpyrazole class of cyclooxygenase-2 inhibitors: Identification of 4-[5-(4-Methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzene sulfonamide (SC-58635 Celecoxib). J. Med. Chem. 1997, 40, 1347;
25. (b) Sakya, S. M.; Rast, B. |Efficient synthesis of 5-alkyl amino and thioether substituted pyrazoles. Tetrahedron Lett. 2003, 44, 7629;
26. (c) Zouaoui, E.; El Gaied, M. M. Synthesis of trifluoromethyl heterocyclic compounds. J. Chem. Res. Synopo. 2003, 4, 242.
27. (a) Souza, F. R.; Souza, V. T.; Ratzlaff, V.; Borges, L. P.; Oliveira, M. R.; Bonacorso, H. G.; Zanatta, N.; Martins, M. A. P.; Mello, C. F. Hypothermic and antipyretic effects of 3-methyl-and3-phenyl-5-hydroxy-5-trichloromethyl-4,5- dihydro-1H-pyrazole-1-carboxamides in mice. Eur. J. Pharmacol. 2002, 451, 141;
28. 2-adrenoceptors and 5-HT receptors mediate the antinociceptive effect of new pyrazolines, but not of dipyrone. Eur. J. Pharmacol. 2004, 496, 93;
29. (c) Tabarelli, Z.; Rubin, M. A.; Berlese, D. B.; Sauzem, P. D.; Missio, T. P.; Teixeira, M. V.; Sinhorin, A. P.; Martins, M. A. P.; Zanatta, N.; Bonacorso, H. G.; Mello, C. F. A pyrazolyl-thiazole derivative causes antinoception in mice. Braz. J. Med. Biol. Res. 2005, 37, 1531.
30. Sauzem, P. D.; Machado, P.; Rubin, M. A.; Sant'Anna, G. S.; Faber, H. B.; de Souza, A. H.; Mello, C. F.; Beck, P.; Burrow, R. A.; Bonacorso, H. G.; Zanatta, N.; Martins, M. A. P. Design and microwave-assisted synthesis of 5-trifluoromethyl-4,5-dihydro-1H-pyrazoles: Novel agents with analgesic and anti-inflammatory properties. Eur. J. Med. Chem. 2008, 43, 1237.
31. Kappe, C. O.; Dallinger, D. The impact of microwave synthesis on drug discovery. Nature Rev. Drug Discov. 2006, 5, 51.
32. (a) Martins, M. A. P.; Pereira, C. M. P: Beck, P.; Machado, P.; Brondani, S.; Moura, S.; Teixeira, M. V. M.; Bonacorso, H. G.; Zanatta, N. Microwave-assisted synthesis of 5-trichloromethyl substituted 1-phenyl-1H-pyrazoles and 1,2-dimethylpyrazolium chlorides. Tetrahedron Lett. 2003, 44, 6669;
33. (b) Martins, M. A. P.; Beck, P.; Cunico, W.; Pereira, C. M. P.; Sinhorin, A. P.; Blanco, R. F.; Peres, R.; Bonacorso, H. G.; Zanatta, N. Microwave assisted synthesis of 5-hydroxy-5-trichloromethyl-4,5-dihydroisoxazoles. Tetrahedron Lett. 2002, 43, 7005.
34. Bonacorso, H. G.; Oliveira, M. R.; Wentz, A. P.; Wastowski, A. D.; Oliveira, A. B.; Hörner, M.; Zanatta, N.; Martins, M. A. P. Haloacetylated enol ethers: Regiospecific synthesis and structural determination of stable 5-hydroxy-1Hpyrazolines. Tetrahedron. 1999, 55, 245.
35. (a) Martins, M. A. P.; Bastos, G. P.; Bonacorso, H. G.; Zanatta, N.; Flores, A. F. C.; Siqueira, G. M. Regiospecific acylation of acetals. A convenient method to obtain β-methoxyvinyl trichloromethyl ketones. Tetrahedron Lett. 1999, 40, 4309;
36. (b) Bonacorso, H. G.; Martins, M. A. P.; Bittencourt, S. R. T.; Lourega, R. V.; Zanatta, N.; Flores, A. F. C. Trifluoroacetylation of unsymmetrical ketone acetals: A convenient route to obtain alkyl side chain trifluoromethylated heterocycles. J. Fluorine Chem. 1999, 99, 177-182.