Synthesis of CF<sub>3</sub>-Azafluorenes through the Cascade Reaction of 2<i>H</i>-Imidazoles with CF<sub>3</sub>-Ynones
A concise synthesis of trifluoromethyl (CF<sub>3</sub>)-substituted azafluorenes based on the reaction of 5-aryl-2<i>H</i>-imidazoles with CF<sub>3</sub>-ynones is reported. The reaction proceeds through C-H activation-initiated formal [3+2] cycloaddition to give spiro[imidazole-4,1'-indene] as a key intermediate, followed by its retro [3+2] cycloaddition, isomerization, and enamine nucleophilic addition. This synthesis of CF<sub>3</sub>-azafluorene derivatives via simultaneous formation of both the indene and the pyridine scaffolds through cascade C-H/C-C/C-N bond cleavage and C≡C bond formation has not been disclosed before. Moreover, the products thus obtained showed antiproliferative activity against cancer cell lines.
Authors
- Shengnan Yan
- Xuesen Fan (ORCID: https://orcid.org/0000-0002-2040-6919)
- Chunhua Ma (ORCID: https://orcid.org/0000-0001-7613-6471)
- Hao Li (ORCID: https://orcid.org/0000-0001-6896-8550)
- Xinying Zhang (ORCID: https://orcid.org/0000-0002-3416-4623)
Institutions
- Henan Normal University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-11-25
- DOI
- https://doi.org/10.1021/acs.orglett.4c03876
- Citations
- 15
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 3.12
Funders
- Higher Education Discipline Innovation Project
- Henan Key Laboratory of Organic Functional Molecules and Drug Innovation