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2-(5-Arylterphenyl-4-yl)quinolines from 2-methylquinoline and 1-(het)aryl-3-phenylprop-2-yn-1-ones in just a one step: A miracle of molecular interplay

Boris Aleksandrovich Trofimov 1
Boris Aleksandrovich Trofimov
,  , 
Lina Pavlovna Nikitina 1
Lina Pavlovna Nikitina
, 
Andrei Valer'evich Afonin 1
Andrei Valer'evich Afonin
, 
Alexander Valentinovich Vashchenko 1
Alexander Valentinovich Vashchenko
10.1016/j.mencom.2018.05.012
Published 2018-04-27
Communication , Volume 28, Issue 3, 267-269
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Trofimov B. A. et al. 2-(5-Arylterphenyl-4-yl)quinolines from 2-methylquinoline and 1-(het)aryl-3-phenylprop-2-yn-1-ones in just a one step: A miracle of molecular interplay // Mendeleev Communications. 2018. Vol. 28. No. 3. pp. 267-269.
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Trofimov B. A., Belyaeva K. V., Nikitina L. P., Afonin A. V., Vashchenko A. V. 2-(5-Arylterphenyl-4-yl)quinolines from 2-methylquinoline and 1-(het)aryl-3-phenylprop-2-yn-1-ones in just a one step: A miracle of molecular interplay // Mendeleev Communications. 2018. Vol. 28. No. 3. pp. 267-269.
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TY - JOUR
DO - 10.1016/j.mencom.2018.05.012
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.05.012
TI - 2-(5-Arylterphenyl-4-yl)quinolines from 2-methylquinoline and 1-(het)aryl-3-phenylprop-2-yn-1-ones in just a one step: A miracle of molecular interplay
T2 - Mendeleev Communications
AU - Trofimov, Boris Aleksandrovich
AU - Belyaeva, Kseniya Vasil'evna
AU - Nikitina, Lina Pavlovna
AU - Afonin, Andrei Valer'evich
AU - Vashchenko, Alexander Valentinovich
PY - 2018
DA - 2018/04/27
PB - Mendeleev Communications
SP - 267-269
IS - 3
VL - 28
ER -
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@article{2018_Trofimov,
author = {Boris Aleksandrovich Trofimov and Kseniya Vasil'evna Belyaeva and Lina Pavlovna Nikitina and Andrei Valer'evich Afonin and Alexander Valentinovich Vashchenko},
title = {2-(5-Arylterphenyl-4-yl)quinolines from 2-methylquinoline and 1-(het)aryl-3-phenylprop-2-yn-1-ones in just a one step: A miracle of molecular interplay},
journal = {Mendeleev Communications},
year = {2018},
volume = {28},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.05.012},
number = {3},
pages = {267--269},
doi = {10.1016/j.mencom.2018.05.012}
}
MLA
Cite this
MLA Copy
Trofimov, Boris Aleksandrovich, et al. “2-(5-Arylterphenyl-4-yl)quinolines from 2-methylquinoline and 1-(het)aryl-3-phenylprop-2-yn-1-ones in just a one step: A miracle of molecular interplay.” Mendeleev Communications, vol. 28, no. 3, Apr. 2018, pp. 267-269. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.05.012.

Abstract

2-Methylquinoline reacts with 1-(het)aryl-3-phenylprop-2-yn-1-ones under mild transition metal-free conditions (55–60°C, 20 mol% KOH, H2O, MeCN) to afford 2-{5’-(het)aryl[1,1’ : 3’,1”]terphenyl-4’-yl}quinolines in up to 35% yield. The reaction likely proceeds via the intermediate 1,3-dipole followed by the double nucleophilic vinylation of the methyl group with two molecules of ynone and subsequent elimination of (het)arenecarboxylic acid.

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