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Mendeleev Commun., 2025 Volume 35, Issue 4, Pages 457–460 (Mi mendc5579)

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

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.

Keywords: alkyne, functionalization, isoquinoline, m-terphenyl, zwitteriones.

Received: 28.11.2024
Accepted: 20.01.2025

Language: English

DOI: 10.71267/mencom.7695



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© Steklov Math. Inst. of RAS, 2025