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Synthesis of polyfluorinated arylhydrazines, arylhydrazones and 3-methyl-1-aryl-1H-indazoles. / Politanskaya, Larisa; Bagryanskaya, Irina; Tretyakov, Evgeny.

In: Journal of Fluorine Chemistry, Vol. 214, 01.10.2018, p. 48-57.

Research output: Contribution to journal › Article › peer-review

Harvard

Politanskaya, L, Bagryanskaya, I & Tretyakov, E 2018, 'Synthesis of polyfluorinated arylhydrazines, arylhydrazones and 3-methyl-1-aryl-1H-indazoles', Journal of Fluorine Chemistry, vol. 214, pp. 48-57. https://doi.org/10.1016/j.jfluchem.2018.06.011

APA

Politanskaya, L., Bagryanskaya, I., & Tretyakov, E. (2018). Synthesis of polyfluorinated arylhydrazines, arylhydrazones and 3-methyl-1-aryl-1H-indazoles. Journal of Fluorine Chemistry, 214, 48-57. https://doi.org/10.1016/j.jfluchem.2018.06.011

Vancouver

Politanskaya L, Bagryanskaya I, Tretyakov E. Synthesis of polyfluorinated arylhydrazines, arylhydrazones and 3-methyl-1-aryl-1H-indazoles. Journal of Fluorine Chemistry. 2018 Oct 1;214:48-57. doi: 10.1016/j.jfluchem.2018.06.011

Author

Politanskaya, Larisa ; Bagryanskaya, Irina ; Tretyakov, Evgeny. / Synthesis of polyfluorinated arylhydrazines, arylhydrazones and 3-methyl-1-aryl-1H-indazoles. In: Journal of Fluorine Chemistry. 2018 ; Vol. 214. pp. 48-57.

BibTeX

@article{b9d30c9968c849528782c3d641888f0c,
title = "Synthesis of polyfluorinated arylhydrazines, arylhydrazones and 3-methyl-1-aryl-1H-indazoles",
abstract = "Polyfluorinated arylhydrazones were synthesized starting from 1-(4-amino-tetrafluorophenyl)ethanone and polyfluorinated arylhydrazines by action of p-toluenesulfonic acid in good yields. The resulting mixtures of E- and Z-isomers were next treated with K2CO3 in MeCN at room temperature. Under these mild reaction conditions Z-isomers underwent intramolecular nucleophilic cyclization to form 3-methyl-1-aryl-1H-indazole derivatives, while E-isomers were not active and were isolated unchanged. Molecular and crystal structures of prepared polyfluorinated (E)-arylhydrazones as well as selected 3-methyl-1-aryl-1H-indazoles were solved by the X-ray diffraction analysis. Meanwhile, the polyfluorinated acetophenone reacted with hydrazine in THF in the absence of a catalyst through a condensation–nucleophilic substitution cascade process to form a 3-methyl-1H-indazole derivative in excellent yield.",
keywords = "(E)-arylhydrazones, 1H-indazole derivatives, C-F activation, p-TSA-induced condensation, Polyfluorinated arylhydrazines, Polyfluorinated azaheterocycles, CYTOTOXICITY EVALUATION, EFFICIENT SYNTHESIS, REPLACEMENT, 1-ARYL-1H-INDAZOLES, 2-BROMOBENZALDEHYDES, POTENT, INDAZOLE, INTRAMOLECULAR AMINATION REACTION, INHIBITORS, DERIVATIVES",
author = "Larisa Politanskaya and Irina Bagryanskaya and Evgeny Tretyakov",
note = "Publisher Copyright: {\textcopyright} 2018 Elsevier B.V.",
year = "2018",
month = oct,
day = "1",
doi = "10.1016/j.jfluchem.2018.06.011",
language = "English",
volume = "214",
pages = "48--57",
journal = "Journal of Fluorine Chemistry",
issn = "0022-1139",
publisher = "Elsevier",

}

RIS

TY - JOUR

T1 - Synthesis of polyfluorinated arylhydrazines, arylhydrazones and 3-methyl-1-aryl-1H-indazoles

AU - Politanskaya, Larisa

AU - Bagryanskaya, Irina

AU - Tretyakov, Evgeny

N1 - Publisher Copyright: © 2018 Elsevier B.V.

PY - 2018/10/1

Y1 - 2018/10/1

N2 - Polyfluorinated arylhydrazones were synthesized starting from 1-(4-amino-tetrafluorophenyl)ethanone and polyfluorinated arylhydrazines by action of p-toluenesulfonic acid in good yields. The resulting mixtures of E- and Z-isomers were next treated with K2CO3 in MeCN at room temperature. Under these mild reaction conditions Z-isomers underwent intramolecular nucleophilic cyclization to form 3-methyl-1-aryl-1H-indazole derivatives, while E-isomers were not active and were isolated unchanged. Molecular and crystal structures of prepared polyfluorinated (E)-arylhydrazones as well as selected 3-methyl-1-aryl-1H-indazoles were solved by the X-ray diffraction analysis. Meanwhile, the polyfluorinated acetophenone reacted with hydrazine in THF in the absence of a catalyst through a condensation–nucleophilic substitution cascade process to form a 3-methyl-1H-indazole derivative in excellent yield.

AB - Polyfluorinated arylhydrazones were synthesized starting from 1-(4-amino-tetrafluorophenyl)ethanone and polyfluorinated arylhydrazines by action of p-toluenesulfonic acid in good yields. The resulting mixtures of E- and Z-isomers were next treated with K2CO3 in MeCN at room temperature. Under these mild reaction conditions Z-isomers underwent intramolecular nucleophilic cyclization to form 3-methyl-1-aryl-1H-indazole derivatives, while E-isomers were not active and were isolated unchanged. Molecular and crystal structures of prepared polyfluorinated (E)-arylhydrazones as well as selected 3-methyl-1-aryl-1H-indazoles were solved by the X-ray diffraction analysis. Meanwhile, the polyfluorinated acetophenone reacted with hydrazine in THF in the absence of a catalyst through a condensation–nucleophilic substitution cascade process to form a 3-methyl-1H-indazole derivative in excellent yield.

KW - (E)-arylhydrazones

KW - 1H-indazole derivatives

KW - C-F activation

KW - p-TSA-induced condensation

KW - Polyfluorinated arylhydrazines

KW - Polyfluorinated azaheterocycles

KW - CYTOTOXICITY EVALUATION

KW - EFFICIENT SYNTHESIS

KW - REPLACEMENT

KW - 1-ARYL-1H-INDAZOLES

KW - 2-BROMOBENZALDEHYDES

KW - POTENT

KW - INDAZOLE

KW - INTRAMOLECULAR AMINATION REACTION

KW - INHIBITORS

KW - DERIVATIVES

UR - http://www.scopus.com/inward/record.url?scp=85051141300&partnerID=8YFLogxK

U2 - 10.1016/j.jfluchem.2018.06.011

DO - 10.1016/j.jfluchem.2018.06.011

M3 - Article

AN - SCOPUS:85051141300

VL - 214

SP - 48

EP - 57

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

SN - 0022-1139

ER -

ID: 16064666