128694-63-3Relevant academic research and scientific papers
Direct [3+2]-cycloaddition of electron-deficient alkynes with CF3CHN2: Regioselective one-pot synthesis of 3-trifluoromethylpyrazoles
Li, Feng,Wang, Jingjing,Pei, Wenlong,Li, Hong,Zhang, Huiling,Song, Manman,Guo, Linyun,Zhang, Anan,Liu, Lantao
, p. 4344 - 4347 (2017)
A direct and facile cycloaddition reaction of electron-deficient terminal alkynes with 2,2,2-trifluorodiazoethane under mild conditions to afford a series of 5-substituted 3-trifluoromethylpyrazoles in high yields is described. The potential application of this cycloaddition reaction was demonstrated via the efficient synthesis of a key intermediate of the antiviral drug AS-136A and a fluorinated analog of Tebufenpyrad.
Practical synthetic method for functionalized 1-methyl-3/5-(trifluoromethyl)-1H-pyrazoles
Tairov, Maxim A.,Levchenko, Vitalina,Stadniy, Ivan A.,Dmytriv, Yurii V.,Dehtiarov, Serhii O.,Kibalnyi, Mykola O.,Melnyk, Anton V.,Veselovych, Stanislav Y.,Borodulin, Yurii V.,Kolotilov, Sergey V.,Ryabukhin, Sergey V.,Volochnyuk, Dmitriy M.
, p. 2619 - 2632 (2020/12/29)
A new, high-yielding, and practical method for synthesis of 1-methyl-3-(trifluoromethyl)-1H-pyrazole and 1-methyl- 5-(trifluoromethyl)-1H-pyrazole, key intermediates for important building blocks relevant to medicinal and agrochemistry, is developed. A one-step procedure for synthesis of the regioisomeric mixture of target pyrazoles was proposed starting from 4-ethoxy- 1,1,1-trifluoro-3-buten-2-one. The procedure for separation of this mixture was elaborated on the basis of the boiling point vs pressure diagram analysis. The efficient synthetic strategies for regioisomeric building blocks bearing CF3 groups at the 3rd and 5th positions were demonstrated. A set of 1-methyl-3-(trifluoromethyl)-1H-pyrazoles containing such a functional group as aldehyde, acid, boron pinacolate, lithium sulfinate, and sulfonyl chloride was synthesized based on lithiation of 1-methyl-3-(trifluoromethyl)- 1H-pyrazole in a flow reactor. Bromination of both 1-methyl-3-(trifluoromethyl)-1H-pyrazole and 1-methyl-5-(trifluoromethyl)-1Hpyrazole by NBS in mild conditions was performed. The introduction of the functional group at the 4th position of 1-methyl-5- (trifluoromethyl)-1H-pyrazole was illustrated by the optimized synthesis of the corresponding aldehyde and acid based on the Br-Li exchange in an appropriate bromide. Alternatively, the introduction of the functional group (acid and boron pinacolate) at the 5th position of 1-methyl-5-(trifluoromethyl)-1H-pyrazole was performed based on the direct ortho-metalation (DoM) reaction of 4- bromo-1-methyl-5-(trifluoromethyl)pyrazole followed by catalytic reductive debromination.
Regioselective Synthesis of Functionalized 3- or 5-Fluoroalkyl Isoxazoles and Pyrazoles from Fluoroalkyl Ynones and Binucleophiles
Chalyk, Bohdan A.,Khutorianskyi, Andrii,Lysenko, Andrii,Fil, Yulia,Kuchkovska, Yuliya O.,Gavrilenko, Konstantin S.,Bakanovych, Iulia,Moroz, Yurii S.,Gorlova, Alina O.,Grygorenko, Oleksandr O.
supporting information, p. 15212 - 15225 (2019/11/19)
A facile synthetic route toward either 3- or 5-fluoroalkyl-substituted isoxazoles or pyrazoles containing an additional functionalization site was developed and applied on a multigram scale. The elaborated approach extends the scope of fluoroalkyl substituents for introduction into the heterocyclic moiety, and uses convenient transformations of the side chain for incorporation of fluoroalkyl-substituted azoles into the structures of biologically active molecules. The utility of the obtained building blocks for isosteric replacement of alkyl-substituted isoxazole and pyrazole was shown by the synthesis of fluorinated Isocarboxazid and Mepiprazole analogues.
Silver-mediated cycloaddition of alkynes with CF3CHN 2: Highly regioselective synthesis of 3-trifluoromethylpyrazoles
Li, Feng,Nie, Jing,Sun, Long,Zheng, Yan,Ma, Jun-An
supporting information, p. 6255 - 6258 (2013/07/05)
Silver screen: The title reaction provides a convenient and efficient method for the construction of 5-substituted 3-trifluoromethylpyrazoles under mild reaction conditions. By using this protocol, the marketed drug Celecoxib (antiarthritic) could be easily synthesized (see scheme; DMF=N,N- dimethylformamide). Copyright
PARAMYXOVIRUS FAMILY INHIBITORS AND METHODS OF USE THEREOF
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Page/Page column 4; 11, (2011/07/08)
Embodiments of the present disclosure include methods for identifying a compound or compounds useful as therapeutic agents in the treatment of paramyxovirus infections, compounds for the treatment of measles, and high throughput screening methods for iden
Improved regioselectivity in pyrazole formation through the use of fluorinated alcohols as solvents: Synthesis and biological activity of fluorinated tebufenpyrad analogs
Fustero, Santos,Roman, Raquel,Sanz-Cervera, Juan F.,Simon-Fuentes, Antonio,Cunat, Ana C.,Villanova, Salvador,Murguia, Marcelo
, p. 3523 - 3529 (2008/09/20)
(Chemical Equation Presented) The preparation of N-methylpyrazoles is usually accomplished through reaction of a suitable 1,3-diketone with methylhydrazine in ethanol as the solvent. This strategy, however, leads to the formation of regioisomeric mixtures of N-methylpyrazoles, which sometimes are difficult to separate. We have determined that the use of fluorinated alcohols such as 2,2,2-trifluoroethanol (TFE) and 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as solvents dramatically increases the regioselectivity in the pyrazole formation, and we have used this modification in a straightforward synthesis of fluorinated analogs of Tebufenpyrad with acaricide activity.
HYDRAZIDE COMPOUND AND PESTICIDAL USE OF THE SAME
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Page/Page column 486-487, (2008/06/13)
A hydrazide compound represented by the formula (1): has excellent pesticidal activity.
Insecticidal anthranilic diamides: A new class of potent ryanodine receptor activators
Lahm, George P.,Selby, Thomas P.,Freudenberger, John H.,Stevenson, Thomas M.,Myers, Brian J.,Seburyamo, Gilles,Smith, Ben K.,Flexner, Lindsey,Clark, Christopher E.,Cordova, Daniel
, p. 4898 - 4906 (2007/10/03)
A novel class of anthranilic diamides has been discovered with exceptional insecticidal activity on a range of Lepidoptera. These compounds have been found to exhibit their action by release of intracellular Ca2+ stores mediated by the ryanodine receptor. The discovery, synthesis, structure-activity, and biological results are presented.
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.
Process for preparing pyrazolecarboxylic acid compounds
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, (2008/06/13)
There is disclosed a process for preparing a pyrazolecarboxylic acid derivative represented by the formula (II): STR1 wherein Y and Z each represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, COOR1, NR1 R2, CONR1 R2, SR1, SO2 NR1 R2, SO2 R3, R3 CO, OR4, CHX2 or CX3 ; A represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridyl group or OR5 ; where R1 and R2 each represent a hydrogen atom or an alkyl group having 1 to 10 carbon atoms; R3 represents an alkyl group having 1 to 10 carbon atoms; R4 represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted phenyl group, CHF2, CF3 or CF3 CH2 ; R5 represents an alkyl group having 1 to 10 carbon atoms; and X represents a halogen atom, which comprises oxidizing a pyrazole compound represented by the formula (I): STR2 wherein Y, Z and A have the same meanings as defined above, with an oxygen-containing gas in the presence of a metal compound catalyst.
