Brønsted Acid‐Promoted Tandem Cyclization/Addition of Enaminones with H‐Phosphine Oxides for Synthesis of C2‐Phosphorylated 2,3‐2<i>H</i>‐Chromones

A facile and efficient protocol to synthesize C2‐phosphorylated 2,3‐2 H ‐chromones is discovered via Brønsted acid‐promoted tandem addition/cyclization of enaminones with H‐phosphine oxides. The reaction exhibits a broad scope, good functional group tolerance, and good yields, and features ability of a gram‐scaled synthesis. Results of mechanistic study reveal that the reaction initially undergoes intramolecular cyclization to form chromone 5 , which can subsequently be reacted with 2a to yield C2‐phosphorylated 2,3‐2 H ‐chromones through intermolecular addition.

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2025-03-24
DOI
https://doi.org/10.1002/ejoc.202500312
Citations
2
Primary Topic
Synthesis of Organic Compounds
Type
article
Field-Weighted Citation Impact
2.79
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article

Brønsted Acid‐Promoted Tandem Cyclization/Addition of Enaminones with H‐Phosphine Oxides for Synthesis of C2‐Phosphorylated 2,3‐2H‐Chromones

You‐Ping Tian, Zhen Yao, Lu-Peng Qi, Qiang Huang et al.
2 citations
European Journal of Organic Chemistry
Synthesis of Organic Compounds
2.79
article

Brønsted Acid‐Promoted Tandem Cyclization/Addition of Enaminones with H‐Phosphine Oxides for Synthesis of C2‐Phosphorylated 2,3‐2H‐Chromones

You‐Ping Tian, Zhen Yao, Lu-Peng Qi, Qiang Huang, Huabin Wang, Qiaoli Li, Ying Zhou, Min Hao, Bi Tang
article en
2 citations

Abstract

A facile and efficient protocol to synthesize C2‐phosphorylated 2,3‐2 H ‐chromones is discovered via Brønsted acid‐promoted tandem addition/cyclization of enaminones with H‐phosphine oxides. The reaction exhibits a broad scope, good functional group tolerance, and good yields, and features ability of a gram‐scaled synthesis. Results of mechanistic study reveal that the reaction initially undergoes intramolecular cyclization to form chromone 5 , which can subsequently be reacted with 2a to yield C2‐phosphorylated 2,3‐2 H ‐chromones through intermolecular addition.

European Journal of Organic ChemistryVol. 28(25)
Guizhou University (CN), Zunyi Medical University (CN)
Openalex Percentile: Top 12%
Synthesis of Organic Compounds
2.79
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Brønsted Acid‐Promoted Tandem Cyclization/Addition of Enaminones with H‐Phosphine Oxides for Synthesis of C2‐Phosphorylated 2,3‐2<i>H</i>‐Chromones — You‐Ping Tian, Zhen Yao, et al. · European Journal of Organic Chemistry (2025) | TGRS Research Map | TGRS