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

Research output: Contribution to journalArticleResearchpeer-review

1 Citation (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 languageEnglish
Pages (from-to)673-681
Number of pages9
JournalAustralian Journal of Chemistry
Volume71
Issue number9
DOIs
Publication statusPublished - 19 Jun 2018

Cite this

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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}",
year = "2018",
month = "6",
day = "19",
doi = "10.1071/CH18191",
language = "English",
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pages = "673--681",
journal = "Australian Journal of Chemistry",
issn = "0004-9425",
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number = "9",

}

Brønsted acid-catalysed allylic amination of 1-(2-aminoaryl)prop-2-en-1-ols to 1,2-dihydroquinolines. / Day, David Philip; Henry, Stuart Adam; Zhao, Yichao; Jin, Jianwen; Clarkson, Guy James; Chan, Philip Wai Hong.

In: Australian Journal of Chemistry, Vol. 71, No. 9, 19.06.2018, p. 673-681.

Research output: Contribution to journalArticleResearchpeer-review

TY - JOUR

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

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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U2 - 10.1071/CH18191

DO - 10.1071/CH18191

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JF - Australian Journal of Chemistry

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