Dezembro 2013 vol. 1 num. 2 - Brazilian Meeting on Organic Synthesis 2013

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New one-pot and regioselective method for the synthesis of 3-trifluoromethyl-1H-1-phenylpyrazoles

Pittaluga, Everton P. ; (PQ)*, Helio G. Bonacorso ; Correa, Michele S. ; Porte, Liliane M. F. ; Junges, Andrizia F. ; Martins, Marcos A. P. ; Zanatta, Nilo ;

Abstract:

Pyrazoles derivatives has been extensively explored by our research group contemplating their biological activities. Efficient approaches to introduce a CF3 group at the C-3 position of pyrazole ring in a regioselective manner has been getting attention, mostly because these compounds often show pharmacological activities such as the antiinflammatory Celecoxib® and the anticoagulant Razaxaban® and the anticoagulant Razaxaban®. So, we report an efficient and regioselective insertion of a CF3 group into pyrazole rings from the reaction of 4-alkoxy-1,1,1-trifluoroalk-3-en-2-ones [CF3C(O)CH =CR1(OR) where R = Me or Et, R1 = H, Me, Ph, 2-Furyl and R1-R2 = -C4H8-] (1a-e) and 1-phenylsemicarbazide (2) in order to obtain 3-trifluoromethyl- 1-phenylpyrazoles (3a-e) as the main isomer.

Abstract:

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Palavras-chave: 3-Trifluoromethylpyrazoles, Cyclization reactions, Phenylsemicarbazides,

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DOI: 10.5151/chempro-15bmos-BMOS2013_2013925215748

Referências bibliográficas
  • [1] 1(a)Bonacorso, H. G.; Pittaluga, E. P.; Alves, S. H.; Schaffer, L. F.;
  • [2] Cavinatto, S.; Porte, L. M. F.; Paim, G. R.; Martins, M. A. P.; Zanatta, N.
  • [3] ARKIVOC 2012, viii, 62; (b) Bonacorso, H. G.; Cavinatto, S.; Campos, P.
  • [4] T.; Porte, L. M. F.; Navarini, J.; Paim, G. R.; Martins, M. A. P.; Zanatta, N.;
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  • [6] 2(a) Bonacorso, H. G.; Correa, M. S.; Porte, L. M. F.; Martins, M. A. P.;
  • [7] Zanatta, N. BR Patent deposited on National Institute for Industrial Property
  • [8] - INPI (PI1105807-2) in agreement to Federal University of Santa Maria,
  • [9] 2011; (b) Bonacorso, H. G.; Correa, M. S.; Porte, L. M. F.; Pittaluga, E. P.;
  • [10] Martins, M. A. P.; Zanatta, N. Tetrahedron Lett. 2012, 53, 5488.
  • [11] 3Braibante, M. E. F.; Clar, G.; Martins, M. A. P. J. Heterocycl. Chem. 1993,
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Como citar:

Pittaluga, Everton P.; (PQ)*, Helio G. Bonacorso; Correa, Michele S.; Porte, Liliane M. F.; Junges, Andrizia F.; Martins, Marcos A. P.; Zanatta, Nilo; "New one-pot and regioselective method for the synthesis of 3-trifluoromethyl-1H-1-phenylpyrazoles", p. 287 . In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 2318-4043, DOI 10.5151/chempro-15bmos-BMOS2013_2013925215748

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