Synthesis of Fluorinated Octahydro-2H-Chromenes in the Presence of the BF3·Et2O–H2O Catalytic System

Irina V. Il’ina; Oksana S. Patrusheva; Dina V. Korchagina; Konstantin P. Volcho; Nariman F. Salakhutdinov

doi:10.1007/s10593-020-02743-z

Synthesis of Fluorinated Octahydro-2H-Chromenes in the Presence of the BF₃·Et₂O–H₂O Catalytic System

Irina V. Il’ina, Oksana S. Patrusheva, Dina V. Korchagina, Konstantin P. Volcho, Nariman F. Salakhutdinov

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

Abstract

The synthesis of fluorinated octahydro-2H-chromene was carried out using the Prins reaction between the monoterpenoid (–)-isopulegol and carbonyl compounds in the presence of the BF₃·Et₂O–H₂O system, which acts as both an acid catalyst and a fluorine source. The use of the readily available and easy-to-use BF₃·Et₂O reagent makes this method of obtaining fluorine derivatives simple and practical.

Original language	English
Pages (from-to)	867-874
Number of pages	8
Journal	Chemistry of Heterocyclic Compounds
Volume	56
Issue number	7
DOIs	https://doi.org/10.1007/s10593-020-02743-z
Publication status	Published - 1 Jul 2020

Keywords

acid catalysts
boron trifluoride etherate
chromene
isopulegol
monoterpenes
organofluorine compounds
Prins reaction
REAGENT
ACID
TETRAHYDROPYRANS
ISOPULEGOL
DISCOVERY
PRINS CYCLIZATION
VANILLIN
POTENT ANALGESIC ACTIVITY

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title = "Synthesis of Fluorinated Octahydro-2H-Chromenes in the Presence of the BF3·Et2O–H2O Catalytic System",

abstract = "The synthesis of fluorinated octahydro-2H-chromene was carried out using the Prins reaction between the monoterpenoid (–)-isopulegol and carbonyl compounds in the presence of the BF3·Et2O–H2O system, which acts as both an acid catalyst and a fluorine source. The use of the readily available and easy-to-use BF3·Et2O reagent makes this method of obtaining fluorine derivatives simple and practical.",

keywords = "acid catalysts, boron trifluoride etherate, chromene, isopulegol, monoterpenes, organofluorine compounds, Prins reaction, REAGENT, ACID, TETRAHYDROPYRANS, ISOPULEGOL, DISCOVERY, PRINS CYCLIZATION, VANILLIN, POTENT ANALGESIC ACTIVITY",

author = "Il{\textquoteright}ina, {Irina V.} and Patrusheva, {Oksana S.} and Korchagina, {Dina V.} and Volcho, {Konstantin P.} and Salakhutdinov, {Nariman F.}",

year = "2020",

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doi = "10.1007/s10593-020-02743-z",

language = "English",

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journal = "Chemistry of Heterocyclic Compounds",

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T1 - Synthesis of Fluorinated Octahydro-2H-Chromenes in the Presence of the BF3·Et2O–H2O Catalytic System

AU - Il’ina, Irina V.

AU - Patrusheva, Oksana S.

AU - Korchagina, Dina V.

AU - Volcho, Konstantin P.

AU - Salakhutdinov, Nariman F.

PY - 2020/7/1

Y1 - 2020/7/1

N2 - The synthesis of fluorinated octahydro-2H-chromene was carried out using the Prins reaction between the monoterpenoid (–)-isopulegol and carbonyl compounds in the presence of the BF3·Et2O–H2O system, which acts as both an acid catalyst and a fluorine source. The use of the readily available and easy-to-use BF3·Et2O reagent makes this method of obtaining fluorine derivatives simple and practical.

AB - The synthesis of fluorinated octahydro-2H-chromene was carried out using the Prins reaction between the monoterpenoid (–)-isopulegol and carbonyl compounds in the presence of the BF3·Et2O–H2O system, which acts as both an acid catalyst and a fluorine source. The use of the readily available and easy-to-use BF3·Et2O reagent makes this method of obtaining fluorine derivatives simple and practical.

KW - acid catalysts

KW - boron trifluoride etherate

KW - chromene

KW - isopulegol

KW - monoterpenes

KW - organofluorine compounds

KW - Prins reaction

KW - REAGENT

KW - ACID

KW - TETRAHYDROPYRANS

KW - ISOPULEGOL

KW - DISCOVERY

KW - PRINS CYCLIZATION

KW - VANILLIN

KW - POTENT ANALGESIC ACTIVITY

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U2 - 10.1007/s10593-020-02743-z

DO - 10.1007/s10593-020-02743-z

M3 - Article

AN - SCOPUS:85089725054

VL - 56

SP - 867

EP - 874

JO - Chemistry of Heterocyclic Compounds

JF - Chemistry of Heterocyclic Compounds

SN - 0009-3122

IS - 7

ER -

Synthesis of Fluorinated Octahydro-2H-Chromenes in the Presence of the BF₃·Et₂O–H₂O Catalytic System

Abstract

Keywords

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