New strategy for the regioselective synthesis of 1-phenyl-3-trifluoromethyl-1H-pyrazoles

A regioselective synthesis of 3-trifluoromethyl-1-phenyl-1H-pyrazoles (1,3-isomers) as well as their 1,5-isomers (5-trifluoromethyl-1-phenyl-1H-pyrazoles), is described. The 1,3-isomers were obtained from the reaction of 4-alkoxy-1,1,1-trifluoroalk-3-en-2-ones with arylhydrazones followed by deprote...

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Published inTetrahedron letters Vol. 54; no. 31; pp. 4076 - 4079
Main Authors Zanatta, Nilo, Amaral, Simone S., dos Santos, Josiane M., da Silva, Andréia M.P.W., Schneider, Juliana M.F.M., Fernandes, Liana da S., Bonacorso, Helio G., Martins, Marcos A.P.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 31.07.2013
Elsevier
Subjects
Chemistry
Chemistry, Organic
Hydrolysis
Phenylhydrazones
Physical Sciences
Pyrazole
Pyrazoles
Regioselective synthesis
Science & Technology
Strategy
Synthesis (chemistry)
Tetrahedrons
Trifluoromethyl enones
Trifluoromethylpyrazoles
ANUOUOJREDZJKU-UZTTZOEKSA-N
Regioselective synthesis
Pyrazoles
Phenylhydrazones
Trifluoromethylpyrazoles
Trifluoromethyl enones
POTENT
REGIOSPECIFIC SYNTHESIS
RING
HALOACETYLATED ENOL ETHERS
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Summary:A regioselective synthesis of 3-trifluoromethyl-1-phenyl-1H-pyrazoles (1,3-isomers) as well as their 1,5-isomers (5-trifluoromethyl-1-phenyl-1H-pyrazoles), is described. The 1,3-isomers were obtained from the reaction of 4-alkoxy-1,1,1-trifluoroalk-3-en-2-ones with arylhydrazones followed by deprotective hydrolysis while the 1,5-isomer was obtained by direct cyclocondensation of 4-alkoxy-1,1,1-trifluoroalk-3-en-2-ones with phenylhydrazine. An unequivocal assignment of the 1,3- and 1,5-isomers of the pyrazole products is given.
Bibliography:ObjectType-Article-1
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ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2013.05.103