Brønsted Acid-Catalysed Allylic Amination of 1-(2-Aminoaryl)prop-2-en-1-ols to 1,2-Dihydroquinolines

David Philip Day; Stuart Adam Henry; Yichao Zhao; Jianwen Jin; Guy James Clarkson; Philip Wai Hong Chan

doi:10.1071/CH18191

Brønsted Acid-Catalysed Allylic Amination of 1-(2-Aminoaryl)prop-2-en-1-ols to 1,2-Dihydroquinolines

David Philip Day, Stuart Adam Henry, Yichao Zhao, Jianwen Jin, Guy James Clarkson, Philip Wai Hong Chan (Lead / Corresponding author)

Drug Discovery Unit

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

3 Citations (Scopus)

Abstract

A highly efficient synthetic method to prepare 1,2-dihydroquinolines that relies on trifluoromethanesulfonic acid (TfOH)-catalysed allylic amination of 1-(2-aminoaryl)prop-2-en-1-ols is described. Achieved at a catalyst loading of 0.01 mol-% under mild conditions at room temperature, the reaction was found to be robust, with a wide range of substitution patterns tolerated. The corresponding N-heterocyclic adducts were obtained in good to excellent yields of 45-93 %.

Original language	English
Pages (from-to)	673-681
Number of pages	9
Journal	Australian Journal of Chemistry
Volume	71
Issue number	9
DOIs	https://doi.org/10.1071/CH18191
Publication status	Published - 19 Jun 2018

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title = "Br{\o}nsted Acid-Catalysed Allylic Amination of 1-(2-Aminoaryl)prop-2-en-1-ols to 1,2-Dihydroquinolines",

abstract = "A highly efficient synthetic method to prepare 1,2-dihydroquinolines that relies on trifluoromethanesulfonic acid (TfOH)-catalysed allylic amination of 1-(2-aminoaryl)prop-2-en-1-ols is described. Achieved at a catalyst loading of 0.01 mol-% under mild conditions at room temperature, the reaction was found to be robust, with a wide range of substitution patterns tolerated. The corresponding N-heterocyclic adducts were obtained in good to excellent yields of 45-93 %.",

author = "Day, {David Philip} and Henry, {Stuart Adam} and Yichao Zhao and Jianwen Jin and Clarkson, {Guy James} and Chan, {Philip Wai Hong}",

note = "Funding Information: This work is supported by a Start-Up Grant from the Department of Chemistry, University of Warwick, and a Discovery Project Grant (DP160101682) from the Australian Research Council. Publisher Copyright: {\textcopyright} 2018 CSIRO.",

year = "2018",

month = jun,

day = "19",

doi = "10.1071/CH18191",

language = "English",

volume = "71",

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journal = "Australian Journal of Chemistry",

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T1 - Brønsted Acid-Catalysed Allylic Amination of 1-(2-Aminoaryl)prop-2-en-1-ols to 1,2-Dihydroquinolines

AU - Day, David Philip

AU - Henry, Stuart Adam

AU - Zhao, Yichao

AU - Jin, Jianwen

AU - Clarkson, Guy James

AU - Chan, Philip Wai Hong

N1 - Funding Information: This work is supported by a Start-Up Grant from the Department of Chemistry, University of Warwick, and a Discovery Project Grant (DP160101682) from the Australian Research Council. Publisher Copyright: © 2018 CSIRO.

PY - 2018/6/19

Y1 - 2018/6/19

N2 - A highly efficient synthetic method to prepare 1,2-dihydroquinolines that relies on trifluoromethanesulfonic acid (TfOH)-catalysed allylic amination of 1-(2-aminoaryl)prop-2-en-1-ols is described. Achieved at a catalyst loading of 0.01 mol-% under mild conditions at room temperature, the reaction was found to be robust, with a wide range of substitution patterns tolerated. The corresponding N-heterocyclic adducts were obtained in good to excellent yields of 45-93 %.

AB - A highly efficient synthetic method to prepare 1,2-dihydroquinolines that relies on trifluoromethanesulfonic acid (TfOH)-catalysed allylic amination of 1-(2-aminoaryl)prop-2-en-1-ols is described. Achieved at a catalyst loading of 0.01 mol-% under mild conditions at room temperature, the reaction was found to be robust, with a wide range of substitution patterns tolerated. The corresponding N-heterocyclic adducts were obtained in good to excellent yields of 45-93 %.

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DO - 10.1071/CH18191

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JO - Australian Journal of Chemistry

JF - Australian Journal of Chemistry

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Brønsted Acid-Catalysed Allylic Amination of 1-(2-Aminoaryl)prop-2-en-1-ols to 1,2-Dihydroquinolines

Abstract

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