Three-Component Cycloaddition Reaction of Aryne, Acrylate, and Imine Derivatives: Divergent Synthesis of Hexahydropyrrolo[1,2- <i>a</i> ]quinolines and 1,4-Dihydroquinolines

A novel synthetic strategy toward hexahydropyrrolo[1,2-<i>a</i>]quinolines and 1,4-dihydroquinolines has been demonstrated, involving aryne-enabled three-component reactions with acrylate and imine derivatives. This transition-metal-free three-component cycloaddition reaction is scalable and operates with good functional group compatibility. The proposed reaction pathway is supported by a deuterium-labeling experiment.

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Publication Details

Journal
Organic Letters
Published
2025-10-13
DOI
https://doi.org/10.1021/acs.orglett.5c03900
Primary Topic
Cyclization and Aryne Chemistry
Type
article
Field-Weighted Citation Impact
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article

Three-Component Cycloaddition Reaction of Aryne, Acrylate, and Imine Derivatives: Divergent Synthesis of Hexahydropyrrolo[1,2- a ]quinolines and 1,4-Dihydroquinolines

Chuanjun Song, Xin Wang, Yanyan Zhu, Wenbo Cai
Organic Letters
Cyclization and Aryne Chemistry
article

Three-Component Cycloaddition Reaction of Aryne, Acrylate, and Imine Derivatives: Divergent Synthesis of Hexahydropyrrolo[1,2- a ]quinolines and 1,4-Dihydroquinolines

Chuanjun Song, Xin Wang, Yanyan Zhu, Wenbo Cai
article en

Abstract

A novel synthetic strategy toward hexahydropyrrolo[1,2-<i>a</i>]quinolines and 1,4-dihydroquinolines has been demonstrated, involving aryne-enabled three-component reactions with acrylate and imine derivatives. This transition-metal-free three-component cycloaddition reaction is scalable and operates with good functional group compatibility. The proposed reaction pathway is supported by a deuterium-labeling experiment.

Organic LettersVol. 27(42)
Zhengzhou University (CN)
Openalex Percentile: Top 78%
Cyclization and Aryne Chemistry
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