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 | |
| Publication status | Published - 19 Jun 2018 |
Cite this
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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 journal › Article › Research › peer-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 %.
UR - http://www.scopus.com/inward/record.url?scp=85049173402&partnerID=8YFLogxK
U2 - 10.1071/CH18191
DO - 10.1071/CH18191
M3 - Article
VL - 71
SP - 673
EP - 681
JO - Australian Journal of Chemistry
JF - Australian Journal of Chemistry
SN - 0004-9425
IS - 9
ER -