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Synthesis of polyfluorinated o-hydroxyacetophenones – convenient precursors of 3-benzylidene-2-phenylchroman-4-ones. / Politanskaya, Larisa; Tretyakov, Evgeny; Xi, Chanjuan.

In: Journal of Fluorine Chemistry, Vol. 229, 109435, 01.2020.

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

Harvard

Politanskaya, L, Tretyakov, E & Xi, C 2020, 'Synthesis of polyfluorinated o-hydroxyacetophenones – convenient precursors of 3-benzylidene-2-phenylchroman-4-ones', Journal of Fluorine Chemistry, vol. 229, 109435. https://doi.org/10.1016/j.jfluchem.2019.109435

APA

Politanskaya, L., Tretyakov, E., & Xi, C. (2020). Synthesis of polyfluorinated o-hydroxyacetophenones – convenient precursors of 3-benzylidene-2-phenylchroman-4-ones. Journal of Fluorine Chemistry, 229, [109435]. https://doi.org/10.1016/j.jfluchem.2019.109435

Vancouver

Politanskaya L, Tretyakov E, Xi C. Synthesis of polyfluorinated o-hydroxyacetophenones – convenient precursors of 3-benzylidene-2-phenylchroman-4-ones. Journal of Fluorine Chemistry. 2020 Jan;229:109435. doi: 10.1016/j.jfluchem.2019.109435

Author

Politanskaya, Larisa ; Tretyakov, Evgeny ; Xi, Chanjuan. / Synthesis of polyfluorinated o-hydroxyacetophenones – convenient precursors of 3-benzylidene-2-phenylchroman-4-ones. In: Journal of Fluorine Chemistry. 2020 ; Vol. 229.

BibTeX

@article{3010c66a950248b79527395c6643968c,
title = "Synthesis of polyfluorinated o-hydroxyacetophenones – convenient precursors of 3-benzylidene-2-phenylchroman-4-ones",
abstract = "A simple and efficient approach to the synthesis of fluorinated o-hydroxyacetophenones in good to excellent yields is reported. We demonstrated a convenient method for replacing the iodine atom in o-iodophenols with MeC(O)-group through the introduction and subsequent hydrolysis of TIPS-CC-moiety by of p-toluenesulfonic acid monohydrate. The resulting compounds may serve as precursors for the synthesis of polyfluorinated 3-benzylidene-2-phenylchroman-4-one derivatives that are of interest as objects for the evaluation of their pharmacological properties.",
keywords = "Aldol reaction, Fluorinated o-iodophenols, Hydration reaction, o-hydroxyacetophenones, Palladium catalysis, Sonogashira coupling, NAPHTHOLS, ACID, DISCOVERY, SOLVENT, PHENOLS, DIRECT ORTHO-ACYLATION, FLUORINE, INHIBITORS",
author = "Larisa Politanskaya and Evgeny Tretyakov and Chanjuan Xi",
note = "The authors thank the Russian Foundation for Basic Research (grant No 19-53-53003) and NSFC (grant No 21911530097) for financial support and the Chemical Service Center SB RAS for spectral and analytical measurements. Publisher Copyright: {\textcopyright} 2019 Elsevier B.V. Copyright: Copyright 2019 Elsevier B.V., All rights reserved.",
year = "2020",
month = jan,
doi = "10.1016/j.jfluchem.2019.109435",
language = "English",
volume = "229",
journal = "Journal of Fluorine Chemistry",
issn = "0022-1139",
publisher = "Elsevier",

}

RIS

TY - JOUR

T1 - Synthesis of polyfluorinated o-hydroxyacetophenones – convenient precursors of 3-benzylidene-2-phenylchroman-4-ones

AU - Politanskaya, Larisa

AU - Tretyakov, Evgeny

AU - Xi, Chanjuan

N1 - The authors thank the Russian Foundation for Basic Research (grant No 19-53-53003) and NSFC (grant No 21911530097) for financial support and the Chemical Service Center SB RAS for spectral and analytical measurements. Publisher Copyright: © 2019 Elsevier B.V. Copyright: Copyright 2019 Elsevier B.V., All rights reserved.

PY - 2020/1

Y1 - 2020/1

N2 - A simple and efficient approach to the synthesis of fluorinated o-hydroxyacetophenones in good to excellent yields is reported. We demonstrated a convenient method for replacing the iodine atom in o-iodophenols with MeC(O)-group through the introduction and subsequent hydrolysis of TIPS-CC-moiety by of p-toluenesulfonic acid monohydrate. The resulting compounds may serve as precursors for the synthesis of polyfluorinated 3-benzylidene-2-phenylchroman-4-one derivatives that are of interest as objects for the evaluation of their pharmacological properties.

AB - A simple and efficient approach to the synthesis of fluorinated o-hydroxyacetophenones in good to excellent yields is reported. We demonstrated a convenient method for replacing the iodine atom in o-iodophenols with MeC(O)-group through the introduction and subsequent hydrolysis of TIPS-CC-moiety by of p-toluenesulfonic acid monohydrate. The resulting compounds may serve as precursors for the synthesis of polyfluorinated 3-benzylidene-2-phenylchroman-4-one derivatives that are of interest as objects for the evaluation of their pharmacological properties.

KW - Aldol reaction

KW - Fluorinated o-iodophenols

KW - Hydration reaction

KW - o-hydroxyacetophenones

KW - Palladium catalysis

KW - Sonogashira coupling

KW - NAPHTHOLS

KW - ACID

KW - DISCOVERY

KW - SOLVENT

KW - PHENOLS

KW - DIRECT ORTHO-ACYLATION

KW - FLUORINE

KW - INHIBITORS

UR - http://www.scopus.com/inward/record.url?scp=85076198965&partnerID=8YFLogxK

U2 - 10.1016/j.jfluchem.2019.109435

DO - 10.1016/j.jfluchem.2019.109435

M3 - Article

AN - SCOPUS:85076198965

VL - 229

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

SN - 0022-1139

M1 - 109435

ER -

ID: 23093849