Convergent synthesis of coumarin C3–C4-fused fluorogenic quinoline scaffolds <i>via</i> aldehyde activation using <i>in situ</i> generated hydrazoic acid

Herein, we report an efficient route for the construction of diversely substituted coumarin C3-C4-fused quinoline from pre-functionalized 4-azido-3-formylcoumarin using various aromatic/heterocyclic amines in excellent yield with a focus on application-oriented substrate scope. This protocol provides straightforward synthesis of fluorogenic coumarin-fused quinoline scaffolds through aldehyde activation using <i>in situ</i> generated HN<sub>3</sub> with excellent atom economy and without any secondary product formation.

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Publication Details

Journal
Organic & Biomolecular Chemistry
Published
2025-01-01
DOI
https://doi.org/10.1039/d5ob00633c
Primary Topic
Click Chemistry and Applications
Type
article
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article

Convergent synthesis of coumarin C3–C4-fused fluorogenic quinoline scaffolds via aldehyde activation using in situ generated hydrazoic acid

K. Sriraghavan, Ranjithkumar Ganesan
Organic & Biomolecular Chemistry
Click Chemistry and Applications
article

Convergent synthesis of coumarin C3–C4-fused fluorogenic quinoline scaffolds via aldehyde activation using in situ generated hydrazoic acid

K. Sriraghavan, Ranjithkumar Ganesan
article en

Abstract

Herein, we report an efficient route for the construction of diversely substituted coumarin C3-C4-fused quinoline from pre-functionalized 4-azido-3-formylcoumarin using various aromatic/heterocyclic amines in excellent yield with a focus on application-oriented substrate scope. This protocol provides straightforward synthesis of fluorogenic coumarin-fused quinoline scaffolds through aldehyde activation using <i>in situ</i> generated HN<sub>3</sub> with excellent atom economy and without any secondary product formation.

Organic & Biomolecular ChemistryVol. 23(27)
Vellore Institute of Technology University (IN)
Openalex Percentile: Top 90%
Click Chemistry and Applications
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