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.
Authors
- Qijian Ni (ORCID: https://orcid.org/0000-0002-3135-1271)
- Qianling Wu
- Xiaojing Wang (ORCID: https://orcid.org/0000-0001-6921-3619)
Institutions
- Anhui Normal University (CN)
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
Funders
- National Natural Science Foundation of China