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One-pot assembly of functionalized (m-terphenyl-4'-yl)isoquinolines from 1-methylisoquinoline and electrophilic acylacetylenes

, 
Lina Pavlovna Nikitina 1
Lina Pavlovna Nikitina
, 
Veronika Sergeevna Saliy 1
Veronika Sergeevna Saliy
, 
Andrei Valer'evich Afonin 1
Andrei Valer'evich Afonin
, 
Igor Alekseevich Ushakov 1
Igor Alekseevich Ushakov
, 
Alexander Valentinovich Vashchenko 1
Alexander Valentinovich Vashchenko
, 
Boris Aleksandrovich Trofimov 1
Boris Aleksandrovich Trofimov
1 A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033 Irkutsk, Russian Federation
10.71267/mencom.7695
Published 2025-05-21
Communication , Volume 35, Issue 4, 457-460
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Belyaeva K. V. et al. One-pot assembly of functionalized (m-terphenyl-4'-yl)isoquinolines from 1-methylisoquinoline and electrophilic acylacetylenes // Mendeleev Communications. 2025. Vol. 35. No. 4. pp. 457-460.
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Belyaeva K. V., Nikitina L. P., Saliy V. S., Afonin A. V., Ushakov I. A., Vashchenko A. V., Trofimov B. A. One-pot assembly of functionalized (m-terphenyl-4'-yl)isoquinolines from 1-methylisoquinoline and electrophilic acylacetylenes // Mendeleev Communications. 2025. Vol. 35. No. 4. pp. 457-460.
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TY - JOUR
DO - 10.71267/mencom.7695
UR - https://mendcomm.colab.ws/publications/10.71267/mencom.7695
TI - One-pot assembly of functionalized (m-terphenyl-4'-yl)isoquinolines from 1-methylisoquinoline and electrophilic acylacetylenes
T2 - Mendeleev Communications
AU - Belyaeva, Kseniya Vasil'evna
AU - Nikitina, Lina Pavlovna
AU - Saliy, Veronika Sergeevna
AU - Afonin, Andrei Valer'evich
AU - Ushakov, Igor Alekseevich
AU - Vashchenko, Alexander Valentinovich
AU - Trofimov, Boris Aleksandrovich
PY - 2025
DA - 2025/05/21
PB - Mendeleev Communications
SP - 457-460
IS - 4
VL - 35
ER -
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@article{2025_Belyaeva,
author = {Kseniya Vasil'evna Belyaeva and Lina Pavlovna Nikitina and Veronika Sergeevna Saliy and Andrei Valer'evich Afonin and Igor Alekseevich Ushakov and Alexander Valentinovich Vashchenko and Boris Aleksandrovich Trofimov},
title = {One-pot assembly of functionalized (m-terphenyl-4'-yl)isoquinolines from 1-methylisoquinoline and electrophilic acylacetylenes},
journal = {Mendeleev Communications},
year = {2025},
volume = {35},
publisher = {Mendeleev Communications},
month = {May},
url = {https://mendcomm.colab.ws/publications/10.71267/mencom.7695},
number = {4},
pages = {457--460},
doi = {10.71267/mencom.7695}
}
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Belyaeva, Kseniya Vasil'evna, et al. “One-pot assembly of functionalized (m-terphenyl-4'-yl)isoquinolines from 1-methylisoquinoline and electrophilic acylacetylenes.” Mendeleev Communications, vol. 35, no. 4, May. 2025, pp. 457-460. https://mendcomm.colab.ws/publications/10.71267/mencom.7695.

Keywords

alkyne
functionalization
isoquinoline
m-terphenyl
zwitteriones.

Abstract

The relative reactivity of deprotonated CH3 group and nitrogen atom of 1-methylisoquinoline towards electrophilic triple bond crucially depends on the acetylene structure and the reaction conditions. 1-Acyl-2-arylacetylenes react with 1-methylisoquinoline in a 2 : 1 molar ratio (34 mol% KOH · 0.5 H2O, H2O/MeCN, 55-60 °C, 24--48 h) to give 1-[5'-(het)aryl-m-terphenyl-4'-yl]isoquinolines in 28--51% yields and 1-[6'-acyl-5'-(het)aryl-m-terphenyl-4'-yl]isoquinolines

in trace to 11% yields. The minor product (proved by X-ray) results from 1,3-shift of the acyl group in the carbanionic intermediate.