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January 23, 2026

Regioselective Annulation of 2‐(2‐Bromophenyl)‐ 1 H ‐Imidazoles With Ortho ‐Substituted Phenylacetylenes Catalyzed by CuI

LWLu‐Yi WangJiangsu Normal University KZKang‐Hao ZhangJiangsu Normal University YZYu‐Tong ZhaiJiangsu Normal University

Key Points

This research aims to explore the regioselective annulation of 2-(2-bromophenyl)-1H-imidazoles with ortho-substituted phenylacetylenes.
Conducted two-component reactions under basic conditions.
Used copper iodide (CuI) as a catalyst.
Examined reactions based on the nature of substituents (electron-withdrawing vs. electron-donating).
Achieved high yields of 5-benzylidene-5H-imidazo[2,1-a]isoindoles when using electron-withdrawing groups.
Obtained 5-arylimidazo[2,1-a]isoquinolines with electron-donating groups.
Reactions indicated distinct mechanisms (5-exo-dig versus 6-endo-dig) based on substituent types.

Abstract

ABSTRACT The two‐component reaction between 2‐(2‐bromophenyl)‐1 H ‐imidazoles and ortho ‐substituted phenylacetylenes was investigated under basic conditions catalyzed by CuI. High yields of 5‐benzylidene‐5 H ‐imidazo2,1‐ a isoindoles were obtained via a 5‐exo‐dig reaction when the substituent was an electron‐withdrawing group. Conversely, when the substituent was an electron‐donating group, the reaction yielded 5‐arylimidazo2,1‐ a isoquinolines through a 6‐endo‐dig process.

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