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

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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

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