Ag(I)-Catalyzed Heterocyclization/[3 + 2] Cycloaddition of α-Alkynylenones with β-Enaminones: Tandem Access to Highly Substituted Cyclopenta[<i>c</i>]furans

A robust Ag(I)-catalyzed tandem heterocyclization/[3 + 2] cycloaddition of α-alkynylenones with β-enaminones was developed, enabling efficient synthesis of cyclopenta[<i>c</i>]furans with good yields, operational simplicity, and broad substrate scope. In addition, it also presents an extended methodology to synthesize unsymmetrical tri(hetero)aryl methane having chromone and furan/pyrrole scaffolds by a slight modification of starting materials. Moreover, the synthesized cyclopenta[<i>c</i>]furans exhibit good fluorescence properties with quantum yields ranging from 0.33 to 0.53, as suggested by the photophysical studies.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-08-25
DOI
https://doi.org/10.1021/acs.joc.5c01707
Primary Topic
Catalytic Alkyne Reactions
Type
article
Field-Weighted Citation Impact
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article

Ag(I)-Catalyzed Heterocyclization/[3 + 2] Cycloaddition of α-Alkynylenones with β-Enaminones: Tandem Access to Highly Substituted Cyclopenta[c]furans

M. Muthukrishnan, Akram A Khan, Kishor R. Thete, Vijay Vara et al.
The Journal of Organic Chemistry
Catalytic Alkyne Reactions
article

Ag(I)-Catalyzed Heterocyclization/[3 + 2] Cycloaddition of α-Alkynylenones with β-Enaminones: Tandem Access to Highly Substituted Cyclopenta[c]furans

M. Muthukrishnan, Akram A Khan, Kishor R. Thete, Vijay Vara, Sera Deepu Panikar
article en

Abstract

A robust Ag(I)-catalyzed tandem heterocyclization/[3 + 2] cycloaddition of α-alkynylenones with β-enaminones was developed, enabling efficient synthesis of cyclopenta[<i>c</i>]furans with good yields, operational simplicity, and broad substrate scope. In addition, it also presents an extended methodology to synthesize unsymmetrical tri(hetero)aryl methane having chromone and furan/pyrrole scaffolds by a slight modification of starting materials. Moreover, the synthesized cyclopenta[<i>c</i>]furans exhibit good fluorescence properties with quantum yields ranging from 0.33 to 0.53, as suggested by the photophysical studies.

The Journal of Organic ChemistryVol. 90(35)
National Chemical Laboratory (IN), Academy of Scientific and Innovative Research (IN)
Openalex Percentile: Top 82%
Catalytic Alkyne Reactions
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