Synthesis of (Hetero)aryl Fused 4 <i>H</i> -Quinolizin-4-ones from <i>N</i> -Ts Substituted (Hetero)arylamides and Pyridotriazoles

This paper describes a practical synthetic method of (hetero)aryl fused 4<i>H</i>-quinolizin-4-ones via (hetero)aryl sp<sup>2</sup> C-H carbenoid functionalization of (hetero)aryl amides using pyridotriazoles with good functional group tolerance. This process demonstrates excellent site-selectivity, enabling the C-H functionalization reaction directed by an amide group by overcoming the interference of strong coordination between <i>N</i>-heterocycles and metal catalysis. The synthetic method represents an efficient strategy with attractive application prospects, including late-stage modification of drug molecules, total synthesis of natural products, and live-cell imaging.

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Publication Details

Journal
Organic Letters
Published
2025-12-09
DOI
https://doi.org/10.1021/acs.orglett.5c04190
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Synthesis of (Hetero)aryl Fused 4 H -Quinolizin-4-ones from N -Ts Substituted (Hetero)arylamides and Pyridotriazoles

Yi Dong, Hua Tian, Xiao-Qiao Hong, Heng Xu et al.
Organic Letters
Catalytic C–H Functionalization Methods
article

Synthesis of (Hetero)aryl Fused 4 H -Quinolizin-4-ones from N -Ts Substituted (Hetero)arylamides and Pyridotriazoles

Yi Dong, Hua Tian, Xiao-Qiao Hong, Heng Xu, Bo Mei, Yiting Chang, Xin Yang
article en

Abstract

This paper describes a practical synthetic method of (hetero)aryl fused 4<i>H</i>-quinolizin-4-ones via (hetero)aryl sp<sup>2</sup> C-H carbenoid functionalization of (hetero)aryl amides using pyridotriazoles with good functional group tolerance. This process demonstrates excellent site-selectivity, enabling the C-H functionalization reaction directed by an amide group by overcoming the interference of strong coordination between <i>N</i>-heterocycles and metal catalysis. The synthetic method represents an efficient strategy with attractive application prospects, including late-stage modification of drug molecules, total synthesis of natural products, and live-cell imaging.

Organic LettersVol. 27(50)
Guiyang Medical University (CN), Chinese Academy of Sciences (CN), Chinese Academy of Medical Sciences & Peking Union Medical College (CN), Peking Union Medical College Hospital (CN), Shanghai Institute of Materia Medica (CN), Institute of Medicinal Plant Development (CN)
Openalex Percentile: Top 70%
Catalytic C–H Functionalization Methods
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