Some New 2-Substituted 5-Trifluoromethylpyridines

Haga, Takahiro; Fujikawa, K.; Koyanagi, Tohru; Nakajima, Toshio; Hayashi, Kouji

doi:10.3987/r-1984-01-0117

Cited by 19 publications

(6 citation statements)

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“…19,20 The synthesized compound is characterized by the presence of a uorine substituent due to the unique properties of uorine-containing compounds in terms of high thermal stability and lipophilicity. 21,22…”

Section: Introductionmentioning

confidence: 99%

Regioselective synthesis and theoretical studies of an anti-neoplastic fluoro-substituted dispiro-oxindole

et al. 2015

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Section: Introductionmentioning

confidence: 99%

Regioselective synthesis and theoretical studies of an anti-neoplastic fluoro-substituted dispiro-oxindole

et al. 2015

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“…e greater antimicrobial activity of compound 1 was attributed to the presence of fluorine atoms in the molecule that promote increased biological activity due to the intrinsic properties of fluorine, small atomic radius, high electronegativity, and stability [12,[38][39][40][41]. e high electronegativity of fluorine may enhance the electrophilicity of neighboring groups in the molecule and the substitution of a methyl group by a trifluoromethyl group, resulting in increased lipophilicity.…”

Section: Resultsmentioning

confidence: 99%

Antimicrobial and Antibiofilm Activities of 4,5-Dihydro-1H-pyrazole-1-carboximidamide Hydrochloride against Salmonella spp.

Damim

Albuquerque

Dantas

et al. 2021

Journal of Chemistry

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In the present study, the antimicrobial and antibiofilm activities of two 4,5-dihydro-1H-pyrazole-1-carboximidamide hydrochloride, (trifluoromethyl) phenyl-substituted (compound 1) and bromophenyl-substituted (compound 2), were evaluated against four Salmonella spp. serotypes through broth microdilution and biofilm-forming activity. Further, the cytotoxicity of the compounds was evaluated by cell viability assays using cultures of HeLa and Vero cell lines, and the mutagenic potential was assessed by the Ames test. In the broth microdilution test, compound 1 inhibited 90% of the strains tested at the minimum inhibitory concentration of 62.5 μg mL−1. Furthermore, both compounds prevented biofilm formation, with a reduction of up to 5.2 log10. HeLa and Vero cells exhibited 100% viability in the presence of compound 1. In contrast, low cell viability was observed in the presence of 15 µg mL−1 of compound 2. Furthermore, no mutagenic potential was detected at any of the tested concentrations of compound 1.

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“…2-Amino-3-chloro-5-(trifluoromethyl)pyridine is readily accessible from the industrially inexpensive 2,3-dichloro-5-(trifluoromethyl)pyridine by simple nucleophilic substitution with ammonia. 9 The N-pivaloyl-protected substrate was treated with two equivalents of LIDA in tetrahydrofuran at -75°C for two hours before the organometallic intermediate was trapped with iodine and benzaldehyde. The deprotected forms of the iodo com-pound 17 and of the alcohol 18 were obtained in 39% and 47% overall yield, respectively (Scheme 6).…”

Section: Derivatization Of 2-amino-3-chloro-5-(trifluoromethyl)pyridinementioning

confidence: 99%

Further Metalations and Functionalizations of Chloro-, Bromo- and Iodo(trifluoromethyl)pyridines

Cottet¹,

Marull²,

Mongin³

et al. 2004

Synthesis

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In accordance with the concept of regioexhaustive functionalization, both 3-chloro-2-(trifluoromethyl)pyridine and 2-bromo-6-(trifluoromethyl)pyridine were converted each time into the three possible carboxylic acids (1, 4 and 5 and 6, 9 and 12, respectively). 2-Bromo-4-(trifluoromethyl)pyridine, 2-bromo-5-(trifluoromethyl)pyridine, 2-iodo-4-(trifluoromethyl)pyridine and 4-iodo-2-(trifluoromethyl)pyridine were selectively deprotonated and subsequently carboxylated at the respective 3-positions thus affording the acids 13-16. Finally, the N-pivaloyl-protected 2-amino-3-chloro-5-(trifluoromethyl)pyridine was deprotonated at the 4-position and the intermediate trapped with iodine and benzaldehyde to provide, after amide cleavage, the aminopyridines 17 and 18.In a preceding article it was demonstrated how the concept of regioexhaustive functionalization 1 can be applied to 2-chloro-5-(trifluoromethyl)pyridine, 2-chloro-6-(trifluoromethyl)pyridine and 3-chloro-4-(trifluoromethyl)pyridine. 2 Taking advantage of the 'toolbox methods', 1 any of the each time three vacant positions was lithiated and the metal was subsequently replaced by an electrophilically delivered substituent (El), in general a carboxy group (Scheme 1, El = COOH).The present article describes the extension of this study to another chloro(trifluoromethyl)pyridine and to a bromo(trifluoromethyl)pyridine. In addition, the direct metalation of two further bromo(trifluoromethyl)pyridines, two iodo(trifluoromethyl)pyridines and of one aminochloro(trifluoromethyl)pyridine are reported.

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Some New 2-Substituted 5-Trifluoromethylpyridines

Cited by 19 publications

References 0 publications

Regioselective synthesis and theoretical studies of an anti-neoplastic fluoro-substituted dispiro-oxindole

Regioselective synthesis and theoretical studies of an anti-neoplastic fluoro-substituted dispiro-oxindole

Antimicrobial and Antibiofilm Activities of 4,5-Dihydro-1H-pyrazole-1-carboximidamide Hydrochloride against Salmonella spp.

Further Metalations and Functionalizations of Chloro-, Bromo- and Iodo(trifluoromethyl)pyridines

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