129585-50-8Relevant academic research and scientific papers
Synthesis of tetra-substituted 5-trifluoromethylpyrazoles via sequential halogenation/palladium-catalyzed C-C and C-N cross-coupling
Wiethan, Carson,Rosa, Wilian C.,Bonacorso, Helio G.,Stradiotto, Mark
, p. 2352 - 2359 (2016)
A mild and efficient protocol for the assembly of tetra-substituted 5-trifluoromethylpyrazoles is presented, involving halogenation at the 4-position of readily prepared tri-substituted 5-trifluoromethylpyrazoles to give 4-halo-1-phenyl-5-trifluoromethyl pyrazoles, and subsequent palladium-catalyzed Negishi or Buchwald-Hartwig cross-couplings to install carbon or nitrogen-based 4-substituents. Key to the success of these challenging cross-couplings is the use of XPhos and JosiPhos CyPF-tBu ligands, respectively.
Novel 4,5-bis(trifluoromethyl)-1H-pyrazoles through a concise sequential iodination-trifluoromethylation reaction
Junges, Andrizia F.,Pittaluga, Everton P.,Zanatta, Nilo,Martins, Marcos A.P.,Bonacorso, Helio G.
, p. 1385 - 1388 (2019/04/30)
An efficient protocol for the assembly of a new series of 1,3-disubstituted 4,5-bis(trifluoromethyl)-1H-pyrazoles – through a concise sequential iodination-trifluoromethylation reaction at the C-4 position of an initial series of 1-aryl-3-(alkyl/aryl)-5-trifluoromethyl-1H-pyrazoles (electronically deactivated heterocycles), using NIS and MFSDA, at good conversion yields and in short reaction times – is reported.
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 (2017/09/23)
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
Method of controlling particular insect pests by applying anthranilamide compounds
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Page/Page column 32, (2015/09/23)
This invention pertains to a method for controlling lepidopteran, homopteran, hemipteran, thysanopteran and coleopteran insect pests comprising contacting the insects or their environment with an arthropodicidally effective amount of a compound of Formula I, its N-oxide or an agriculturally suitable salt thereof wherein A and B and R1 through R8 are as defined in the disclosure. This invention further relates to a benzoxazinone compound of Formula 10 wherein R4 through R8 are as defined in the disclosure, useful for preparation of a compound of Formula I.
Anthranilamide arthropodicide treatment
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Page/Page column 31, (2015/11/27)
This invention pertains to methods for protecting a propagule or a plant grown therefrom from invertebrate pests comprising contacting the propagule or the locus of the propagule with a biologically effective amount of a compound of Formula I, its N-oxide or an agriculturally suitable salt thereof wherein A and B and R1 through R8 are as defined in the disclosure. This invention also relates to propagules treated with a compound of Formula I and compositions comprising a Formula I compound for coating propagules.
A modified and practical synthetic route to indazoles and pyrazoles using tungstate sulfuric acid
Rahmatzadeh, S. Setareh,Karami, Bahador,Khodabakhshi, Saeed
, p. 17 - 20 (2015/02/19)
Tungstate sulfuric acid-catalyzed Knorr reaction have been used as a simple, rapid, atom economic and green method for the synthesis of indazole and pyrazole derivatives based on the condensation of hydrazine derivatives and ss-dicarbonyl compounds under solvent-free conditions. It was found that the catalyst could be recovered and reused without significant loss of its activity. The use of this method provides a novel and improved modification of Knorr synthesis in terms of clean reaction profile, use of a safe catalyst and solvent-free conditions. A green method for the synthesis of indazole and pyrazole derivatives from the condensation of hydrazine derivatives with dicarbonyl compounds has been described. Tungstate sulfuric acid (TSA) catalyzed efficiently the reactions to give good yields.
The effect of pressurized carbon dioxide on the cyclocondensation reaction between 4-alkoxy-1,1,1-trifluoro-3-alken-2-ones and hydrazines
Rossatto, Marcelo,Casanova, Caroline,Lima, Ana P.,Emmerich, Daniel J.,Oliveira, Vladimir,Dallago, Rogerio M.,Frizzo, Clarissa P.,Moreira, Dayse N.,Buriol, Lilian,Brondani, Sergio,Zanatta, Nilo,Bonacorso, Helio G.,Martins, Marcos A. P.
, p. 224 - 232 (2014/03/21)
The synthesis of 1-unsubstituted and 1-phenyl-5-trifluoromethylpyrazoles from the reaction of 4- alkoxy-1,1,1-trifluoro-3-alken-2-ones [CF 3C(O)CH=C(R1)OR, where R = Me, Et and R1 = H, Me, Ph] with hydrazines [NH2NHR2, where R2 = H, Ph] in pressurized carbon dioxide is reported for the first time. Reaction conditions such as pressure, temperature and time were evaluated. The methodology developed herein was suitable to synthesize products in moderate to excellent yields (60 % - 96 %) and short reaction times (15 - 45 min).
Synergic effects of ionic liquid and microwave irradiation in promoting trifluoromethylpyrazole synthesis
Buriol, Lilian,Frizzo, Clarissa P.,Prola, Lizie D. T.,Moreira, Dayse N.,Marzari, Mara R. B.,Scapin, Elisandra,Zanatta, Nilo,Bonacorso, Helio G.,Martins, Marcos A. P.
experimental part, p. 1130 - 1135 (2012/06/18)
The synthesis of 5-trifluoromethyl-1-phenyl-1H-pyrazoles from the reactions of 4-alkoxy-1,1,1-trifluoro-3-alken-2-ones [CF3C(O)CH=C(R 1)OR, where R = Me, Et; R1= H, Me, Bu, i-Bu, Ph, 4-MeC6H4, 4-FCsu
Pyrazole synthesis under microwave irradiation and solvent-free condition
Buriol, Lilian,Frizzo, Clarissa P.,Marzari, Mara R. B.,Moreira, Dayse N.,Prola, Lizie? D. T.,Zanatta, Nilo,Bonacorso, Helio G.,Martins, Marcos A. P.
experimental part, p. 1037 - 1044 (2010/10/21)
This paper presents a study of solvent-free reaction conditions using microwave irradiation (MW) to obtain 4,5-dihydro-1H-pyrazoles and dehydrated pyrazoles by the cyclocondensation reaction of 4-alkoxy-1,1,1-trifuoro-3-alken- 2-ones [CF3C(O)CH=C(R1)OR, where R/R1 = Et/H, Me/Me and Me/Ph] with hydrazines [NH2NH-R2, where R2 = CO2Me, Ph, CH2CH2OH]. Some reactions were performed under the same reaction conditions using methanol as solvent. The results obtained using MW equipment for synthesis under solvent-free conditions were also compared with those described in literature for conventional thermal heating and heating with a domestic MW oven. In general, the products furnished by reaction in MW equipment for synthesis presented better yields and shorter reaction times. In addition, it was demonstrated that the reaction temperature altered the formation of products for each hydrazine showing that MW equipment for synthesis is effcient for reacting hydrazines and 4-alkoxy-1,1,1-trifuoro-3- alken-2-ones to procedure the products 4,5-dihydro-1H-pyrazoles and dehydrated pyrazoles.
Microwave-mediated pyrazole fluorinations using selectfluor
Sloop, Joseph C.,Jackson, James L.,Schmidt, Robert D.
scheme or table, p. 341 - 345 (2010/08/05)
Microwave-mediated electrophilic fluorinations and a new single-pot condensation en route to ring-fluorinated pyrazoles were examined: chemical equation represented The monofluorination by these methods was successful for a variety of pyrazoles, with yields ranging from 13% to 75%. While electrophilic aromatic fluorination of 3-CF3 pyrazoles proved largely ineffective, development ofa single-pot process overcame this limitation. The microwave-mediated reaction is regioselective; ring fluorination of the heterocycle occurs preferentially over phenyl and alkyl substituents. Alkyl side chain fluorination, when desired, can be modulated by reactant ratios. The single-pot method, which involves acid catalysis by H-TEDA, produces 4-fluoropyrazoles products.
