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March 10, 2026European Journal of Organic Chemistry0 citations

Nickel‐Catalyzed Three‐Component Carboamination Tandem Cyclization of Propargyl Alcohols for Assembly of 2,3‐Disubstituted Quinolines

JXJiale XingGuangdong University of Technology ZXZhongke XieGuangdong University of Technology YHYanping HUOGuangdong University of Technology

Key Points

This research aims to develop a new method for the synthesis of 2,3-disubstituted quinolines using a tandem cyclization approach.
Utilized a nickel catalyst for the reaction process.
Executed a three-component approach involving propargyl alcohols, organoboronic acids, and anthranils.
Focused on the formation of an α,β- unsaturated imine intermediate for cyclization.
Successfully synthesized 2,3-disubstituted quinolines with good functional group tolerance.
Demonstrated versatility in producing 2,3-unsymmetrically disubstituted quinolines and 2-vinyl quinolines.

Abstract

A nickel‐catalyzed three‐component carboamination tandem cyclization strategy has been developed for the synthesis of 2,3‐disubstituted quinolines from propargyl alcohols, organoboronic acids, and anthranils. A novel α,β‐unsaturated imine intermediate plays a pivotal role in this system, undergoing base‐mediated annulation to assemble the quinoline core structure. This protocol exhibits good functional group tolerance and can be applied to the synthesis of 2,3‐unsymmetrically disubstituted quinolines and 2‐vinyl quinolines.

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