Silver/Indium-Catalyzed Cyclization of <i>O</i> -Alkynylisocyanobenzenes with Nitriles for the Synthesis of Amide-Substituted Quinolines

An efficient method for the synthesis of amide-substituted quinolines through silver/indium-catalyzed cyclization from <i>o</i>-alkynylisocyanobenzenes with nitriles has been reported. The reaction was initiated by the intramolecular cyclization of the <i>o</i>-alkynylisocyanobenzenes to generate the quinolyl cationic intermediate, followed by an intermolecular Ritter reaction with nitriles to give a nitrile-quinoline-based nitrilium salt, subsequently with hydrolysis to afford the amide-substituted quinolines.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-03-16
DOI
https://doi.org/10.1021/acs.joc.6c00135
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Silver/Indium-Catalyzed Cyclization of O -Alkynylisocyanobenzenes with Nitriles for the Synthesis of Amide-Substituted Quinolines

Shan Luo, Keying Gu, Zhuang Xiong, Jia-Qiang Wu et al.
The Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
article

Silver/Indium-Catalyzed Cyclization of O -Alkynylisocyanobenzenes with Nitriles for the Synthesis of Amide-Substituted Quinolines

Shan Luo, Keying Gu, Zhuang Xiong, Jia-Qiang Wu, Jingjing Liu, Zirou Mai
article en

Abstract

An efficient method for the synthesis of amide-substituted quinolines through silver/indium-catalyzed cyclization from <i>o</i>-alkynylisocyanobenzenes with nitriles has been reported. The reaction was initiated by the intramolecular cyclization of the <i>o</i>-alkynylisocyanobenzenes to generate the quinolyl cationic intermediate, followed by an intermolecular Ritter reaction with nitriles to give a nitrile-quinoline-based nitrilium salt, subsequently with hydrolysis to afford the amide-substituted quinolines.

The Journal of Organic ChemistryVol. 91(12)
Guangzhou Institutes of Biomedicine and Health (CN), University of Chinese Academy of Sciences (CN)
Openalex Percentile: Top 20%
Catalytic C–H Functionalization Methods
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