Brønsted Acid-Catalysed Allylic Amination of 1-(2-Aminoaryl)prop-2-en-1-ols to 1,2-Dihydroquinolines
David Philip Day A , Stuart Adam Henry A , Yichao Zhao B , Jianwen Jin B , Guy James Clarkson A and Philip Wai Hong Chan A B C
+ Author Affiliations
- Author Affiliations
A Department of Chemistry, University of Warwick, Coventry, CV4 7AL, UK.
B School of Chemistry, Monash University, Clayton, Vic. 3800, Australia.
C Corresponding author. Email: phil.chan@monash.edu
Australian Journal of Chemistry 71(9) 673-681 https://doi.org/10.1071/CH18191
Submitted: 29 April 2018 Accepted: 22 May 2018 Published: 19 June 2018
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 %.
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