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

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

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 %.

UR - https://www.scopus.com/pages/publications/85049173402

U2 - 10.1071/CH18191

DO - 10.1071/CH18191

M3 - Article

AN - SCOPUS:85049173402

SN - 0004-9425

VL - 71

SP - 673

EP - 681

JO - Australian Journal of Chemistry

JF - Australian Journal of Chemistry

IS - 9

ER -