Эта публикация цитируется в 1 статье

Communications

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

K. V. Belyaeva, L. P. Nikitina, V. S. Saliy, A. V. Afonin, I. A. Ushakov, A. V. Vashchenko, B. A. Trofimov

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033 Irkutsk, Russian Federation

Аннотация: 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.

Ключевые слова: alkyne, functionalization, isoquinoline, m-terphenyl, zwitteriones.

Поступила в редакцию: 28.11.2024
Принята в печать: 20.01.2025

Язык публикации: английский

DOI: 10.71267/mencom.7695

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