Dearomative Ring-Opening of <i>N</i>-Fused Heteroarenes: Access to Tetrasubstituted Alkenes and Ketimines

We report a novel and efficient strategy for constructing tetrasubstituted alkenes and α-iminonitriles from 3-aminoindolizines and 3-aminoimidazo[1,2-<i>a</i>]pyridines. This approach involves a dearomative ring-opening of <i>N</i>-fused heteroaromatic amines coupled to a DDQ-mediated oxidative process under mild, metal-free conditions. The methodology demonstrates broad substrate scope, excellent functional group tolerance, and scalability, offering a versatile platform for synthesizing complex alkenes and nitrile-containing frameworks.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-04-15
DOI
https://doi.org/10.1021/acs.joc.5c00435
Citations
1
Primary Topic
Synthesis and Reactivity of Heterocycles
Type
article
Field-Weighted Citation Impact
0.94

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article

Dearomative Ring-Opening of N-Fused Heteroarenes: Access to Tetrasubstituted Alkenes and Ketimines

Qijian Ni, Qianling Wu, Xiaojing Wang
1 citations
The Journal of Organic Chemistry
Synthesis and Reactivity of Heterocycles
0.94
article

Dearomative Ring-Opening of N-Fused Heteroarenes: Access to Tetrasubstituted Alkenes and Ketimines

Qijian Ni, Qianling Wu, Xiaojing Wang
article en
1 citations

Abstract

We report a novel and efficient strategy for constructing tetrasubstituted alkenes and α-iminonitriles from 3-aminoindolizines and 3-aminoimidazo[1,2-<i>a</i>]pyridines. This approach involves a dearomative ring-opening of <i>N</i>-fused heteroaromatic amines coupled to a DDQ-mediated oxidative process under mild, metal-free conditions. The methodology demonstrates broad substrate scope, excellent functional group tolerance, and scalability, offering a versatile platform for synthesizing complex alkenes and nitrile-containing frameworks.

The Journal of Organic ChemistryVol. 90(16)
Anhui Normal University (CN)
National Natural Science Foundation of China
Zero hunger
Openalex Percentile: Top 27%
Synthesis and Reactivity of Heterocycles
0.94
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