Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 20
59
Views
4
CrossRef citations to date
0
Altmetric
Original Articles

Simplified Approach to the Regiospecific Synthesis of Trichloromethylpyrazolines Using Microwave Irradiation

, , , , , & show all
Pages 3465-3476 | Received 26 Dec 2007, Published online: 30 Sep 2008

REFERENCES

  • 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 .
  • 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 .
  • 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 .
  • 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 .
  • 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 .
  • Lautens , M. ; Roy , A. synthetic studies of the formation of oxazoles and isoxazoles from N-acetoacetyl derivatives: Scope and limitations. Org. Lett. 2002, 555.
  • Padwa , A. 1,3-dipolar cycloaddition chemistry ; John Wiley & Sons : New York , 1984 ; vol. 1 ; (b) Bohrisch, J.; Patzel, M.; Mugge, C.; Liebscher, J. Ring transformation by ring chain transfer VI1: Regioselective synthesis of (ω-Aminoalkyl)pyrazoles from semicyclic 3-chloro-2-propeniminium salts and hydrazines. Synthesis. 1991, 1153; (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; (d) Katritzky, A. R.; Wang, M.; Zhang, S.; Voronkov, M. V. Regioselective synthesis of polysubstituted pyrazoles and isoxazoles. J. Org. Chem. 2001, 66, 6787.
  • (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 ; (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; (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; (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 .
  • 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 .
  • 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 .
  • (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 ; ( b ) Spiegler , W. Götz , N. Fine einfache Synthese von Isoxazol-5-carbonsäure . Synthesis 1986 , 1 , 69 ; ( 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 .
  • 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 .
  • 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 .
  • 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 .
  • 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.
  • (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]benzenesulfonamide (SC-58635 Celecoxib) . J. Med. Chem. 1997 , 40 , 1347 ; ( b ) Sakya , S. M. ; Rast , B. Efficient synthesis of 5-alkyl amino and thioether substituted pyrazoles . Tetrahedron Lett . 2003 , 44 , 7629 ; ( c ) Zouaoui , E. ; El Gaied , M. M. Synthesis of trifluoromethyl heterocyclic compounds . J. Chem. Res. Synopo. 2003 , 4 , 242 .
  • (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 ; ( b ) Godoy , M. C. M. ; Fighera , M. R. ; Souza , F. R. ; Flores , A. E. ; Rubin , M. A. ; Oliveira , M. R. ; Zanatta , N. ; Martins , M. A. P. ; Bonacorso , H. G. ; Mello , C. F. α2-adrenoceptors and 5-HT receptors mediate the antinociceptive effect of new pyrazolines, but not of dipyrone . Eur. J. Pharmacol . 2004 , 496 , 93 ; ( 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 .
  • 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 .
  • Kappe , C. O. ; Dallinger , D. The impact of microwave synthesis on drug discovery . Nature Rev. Drug Discov. 2006 , 5 , 51 .
  • (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 ; ( 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 .
  • 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-1H-pyrazolines . Tetrahedron. 1999 , 55 , 245 .
  • (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; ( 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.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.