497833-01-9Relevant academic research and scientific papers
Sequential one-pot three-step synthesis of polysubstituted 4-(5-(trifluoromethyl)-1: H -pyrazol-4-yl)-1 H -1,2,3-triazole systems
Bonacorso, Helio G.,Dal Forno, Gean M.,Wiethan, Carson,Ketzer, Alex,Zanatta, Nilo,Frizzo, Clarissa P.,Martins, Marcos A. P.,Stradiotto, Mark
, p. 43957 - 43964 (2017)
This work reports a successful one-pot three-step protocol for the synthesis of a new series of 15 examples of polysubstituted 4-(5-(trifluoromethyl)-1H-pyrazol-4-yl)-1H-1,2,3-triazoles, in which sequential Sonogashira cross-coupling, desilylation, and a
Regioselective synthesis of 1-aryl-4-bromo-5-trifluoromethylpyrazoles
Nenajdenko,Reznichenko,Balenkova
, p. 172 - 173 (2006)
A novel regioselective route to 1-aryl-4-bromo-5-trifluoromethylpyrazoles involves reactions of arylhydrazines with 3-bromo-4-ethoxy-1,1,1-trifluorobut-3- en-2-one.
Switchable reactivity: The site-selective functionalization of trifluoromethyl-substituted pyrazoles
Schlosser, Manfred,Volle, Jean-Noel,Leroux, Frederic,Schenk, Kurt
, p. 2913 - 2920 (2007/10/03)
Modern organometallic methods enable the regioflexible conversion of simple heterocyclic starting materials into families of isomers and congeners. Depending on the choice of the reagent, 1-methyl-5-(trifluoromethyl)pyrazole (1) undergoes deprotonation and subsequent carboxylation mainly or exclusively at either the 4-position of the heterocycle or at the nitrogen-attached methyl group. Similarly, 1-phenyl-5-(trifluoromethyl)pyrazole (5) and 3-methyl-l-phenyl-5-(trifluoromethyl)pyrazole (8) are selectively attacked by lithium diisopropylamide at the heterocyclic 4-position and by butyllithium concomitantly at the 4-position and the ortho position of the phenyl ring. In contrast, metalation of 1-methyl-3-(trifluoromethyl)pyrazole (2) occurs only at the 5-position, whatever the organometallic or metal amide base. Further sites become accessible to functionalization if bromine is introduced into the heterocyclic or aromatic ring. This has been demonstrated with 4-bromo-1-methyl-5-(trifluoromethyl)pyrazole (3), 4-bromo-l-methyl-3-(trifluoromethyl)pyrazole (4), 4-bromo-1-methyl-5-(trifluoromethyl)pyrazole (7) and 1-(2-bromophenyl)-5-(trifluoromethyl)pyrazole (6). Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
