One-pot synthesis of fluorinated 2-arylchroman-4-one derivatives from 2-(triisopropylsilyl)ethynylphenols and aromatic aldehydes

Larisa Politanskaya; Jiaying Wang; Nadezhda Troshkova; Igor Chuikov; Irina Bagryanskaya

doi:10.1016/j.jfluchem.2022.110045

One-pot synthesis of fluorinated 2-arylchroman-4-one derivatives from 2-(triisopropylsilyl)ethynylphenols and aromatic aldehydes

Larisa Politanskaya, Jiaying Wang, Nadezhda Troshkova, Igor Chuikov, Irina Bagryanskaya

Department of Natural Sciences

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

Abstract

A facile p-toluenesulfonic acid–catalyzed one-pot synthesis of biologically interesting fluorinated 2-arylchroman-4-one derivatives from 2-(triisopropylsilyl)ethynylphenols and aromatic aldehydes is described. This synthetic method is metal-free, operationally simple, cheap and productive. It provides a rapid access to the title compounds as well as their 3-benzylidene and 8-cinnamoyl derivatives, that are of interest as objects for the evaluation of their pharmacological properties.

Original language	English
Article number	110045
Journal	Journal of Fluorine Chemistry
Volume	263
DOIs	https://doi.org/10.1016/j.jfluchem.2022.110045
Publication status	Published - Nov 2022

Keywords

cycloaddition
fluorinated flavanones
hydration reaction
NMR analysis
p-toluenesulfonic acid
TIPS-ethynylphenols

OECD FOS+WOS

1.05 EARTH AND RELATED ENVIRONMENTAL SCIENCES
1.06 BIOLOGICAL SCIENCES
1.04 CHEMICAL SCIENCES

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10.1016/j.jfluchem.2022.110045

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title = "One-pot synthesis of fluorinated 2-arylchroman-4-one derivatives from 2-(triisopropylsilyl)ethynylphenols and aromatic aldehydes",

abstract = "A facile p-toluenesulfonic acid–catalyzed one-pot synthesis of biologically interesting fluorinated 2-arylchroman-4-one derivatives from 2-(triisopropylsilyl)ethynylphenols and aromatic aldehydes is described. This synthetic method is metal-free, operationally simple, cheap and productive. It provides a rapid access to the title compounds as well as their 3-benzylidene and 8-cinnamoyl derivatives, that are of interest as objects for the evaluation of their pharmacological properties.",

keywords = "cycloaddition, fluorinated flavanones, hydration reaction, NMR analysis, p-toluenesulfonic acid, TIPS-ethynylphenols",

author = "Larisa Politanskaya and Jiaying Wang and Nadezhda Troshkova and Igor Chuikov and Irina Bagryanskaya",

note = "Funding Information: The authors thank the Multi-Access Chemical Service Center SB RAS for spectral and analytical measurements, and Ministry of Science and Higher Education of the Russian Federation (Project FWUE-2022-0002) for financial support. Publisher Copyright: {\textcopyright} 2022",

year = "2022",

month = nov,

doi = "10.1016/j.jfluchem.2022.110045",

language = "English",

volume = "263",

journal = "Journal of Fluorine Chemistry",

issn = "0022-1139",

publisher = "Elsevier",

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TY - JOUR

T1 - One-pot synthesis of fluorinated 2-arylchroman-4-one derivatives from 2-(triisopropylsilyl)ethynylphenols and aromatic aldehydes

AU - Politanskaya, Larisa

AU - Wang, Jiaying

AU - Troshkova, Nadezhda

AU - Chuikov, Igor

AU - Bagryanskaya, Irina

N1 - Funding Information: The authors thank the Multi-Access Chemical Service Center SB RAS for spectral and analytical measurements, and Ministry of Science and Higher Education of the Russian Federation (Project FWUE-2022-0002) for financial support. Publisher Copyright: © 2022

PY - 2022/11

Y1 - 2022/11

N2 - A facile p-toluenesulfonic acid–catalyzed one-pot synthesis of biologically interesting fluorinated 2-arylchroman-4-one derivatives from 2-(triisopropylsilyl)ethynylphenols and aromatic aldehydes is described. This synthetic method is metal-free, operationally simple, cheap and productive. It provides a rapid access to the title compounds as well as their 3-benzylidene and 8-cinnamoyl derivatives, that are of interest as objects for the evaluation of their pharmacological properties.

AB - A facile p-toluenesulfonic acid–catalyzed one-pot synthesis of biologically interesting fluorinated 2-arylchroman-4-one derivatives from 2-(triisopropylsilyl)ethynylphenols and aromatic aldehydes is described. This synthetic method is metal-free, operationally simple, cheap and productive. It provides a rapid access to the title compounds as well as their 3-benzylidene and 8-cinnamoyl derivatives, that are of interest as objects for the evaluation of their pharmacological properties.

KW - cycloaddition

KW - fluorinated flavanones

KW - hydration reaction

KW - NMR analysis

KW - p-toluenesulfonic acid

KW - TIPS-ethynylphenols

UR - http://www.scopus.com/inward/record.url?scp=85144133682&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/dfa894c7-b26d-38b2-8998-9ac30d965303/

U2 - 10.1016/j.jfluchem.2022.110045

DO - 10.1016/j.jfluchem.2022.110045

M3 - Article

AN - SCOPUS:85144133682

VL - 263

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

SN - 0022-1139

M1 - 110045

ER -

One-pot synthesis of fluorinated 2-arylchroman-4-one derivatives from 2-(triisopropylsilyl)ethynylphenols and aromatic aldehydes

Abstract

Keywords

OECD FOS+WOS

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