Synthesis of π-Extended Imidazo[1,2-<i>a</i>]quinolines via Carboxylic Acid-Assisted Ru(II)-Catalyzed Dual C–H Activation and Alkyne Annulation

Ru(II)-catalyzed, carboxylic acid-assisted oxidative annulation of <i>N</i>-aryl azoles with alkynes via double C-H activation to produce highly functionalized π-extended imidazo[1,2-<i>a</i>]quinolines is reported. The reaction features a broad substrate generality and tolerates various biologically relevant scaffolds. Interestingly, annulated products showed strong fluorescence properties and an AgIE effect and exhibited a selective fluorescent response toward the Cu<sup>2+</sup> ion. Further photocatalytic properties of the product are demonstrated in the photochemical coupling of azoles and arenes.

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Publication Details

Journal
Organic Letters
Published
2024-11-27
DOI
https://doi.org/10.1021/acs.orglett.4c03522
Citations
8
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
2.00

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article

Synthesis of π-Extended Imidazo[1,2-a]quinolines via Carboxylic Acid-Assisted Ru(II)-Catalyzed Dual C–H Activation and Alkyne Annulation

Nitumoni Hazarika, Monuranjan Konwar, Animesh Das
8 citations
Organic Letters
Catalytic C–H Functionalization Methods
2.00
article

Synthesis of π-Extended Imidazo[1,2-a]quinolines via Carboxylic Acid-Assisted Ru(II)-Catalyzed Dual C–H Activation and Alkyne Annulation

Nitumoni Hazarika, Monuranjan Konwar, Animesh Das
article en
8 citations

Abstract

Ru(II)-catalyzed, carboxylic acid-assisted oxidative annulation of <i>N</i>-aryl azoles with alkynes via double C-H activation to produce highly functionalized π-extended imidazo[1,2-<i>a</i>]quinolines is reported. The reaction features a broad substrate generality and tolerates various biologically relevant scaffolds. Interestingly, annulated products showed strong fluorescence properties and an AgIE effect and exhibited a selective fluorescent response toward the Cu<sup>2+</sup> ion. Further photocatalytic properties of the product are demonstrated in the photochemical coupling of azoles and arenes.

Organic LettersVol. 26(49)
Indian Institute of Technology Guwahati (IN)
Science and Engineering Research Board
Clean water and sanitation
Openalex Percentile: Top 14%
Catalytic C–H Functionalization Methods
2.00
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Synthesis of π-Extended Imidazo[1,2-<i>a</i>]quinolines via Carboxylic Acid-Assisted Ru(II)-Catalyzed Dual C–H Activation and Alkyne Annulation — Nitumoni Hazarika, Monuranjan Konwar, et al. · Organic Letters (2024) | TGRS Research Map | TGRS