Solvent-Regulated Cyclization of Arylidene Isoxazolones with Amidines for Regiodivergent Synthesis of 4- and 5-Acylimidazoles
<i>N</i>-Iodosuccinimide-promoted cascade reactions of arylidene isoxazolones with amidines in <i>p</i>-xylene were accomplished, affording 5-acylimidazoles in good to excellent yields. Interestingly, when the reactions were performed by employing acetonitrile as the solvent, 4-acylimidazoles were efficiently obtained. Mechanistic studies indicate that the formation of imidazolyl and acyl moieties may undergo a spiroannulation-ring opening aromatization-hydrolysis cascade reaction sequence. Based on this solvent-regulated tandem reaction strategy, a powerful protocol for switchable and regiodivergent synthesis of structurally diverse 4-acylimidazoles and 5-acylimidazoles was successfully established.
Authors
- Yi Wu (ORCID: https://orcid.org/0000-0001-5704-2111)
- Hui Xu (ORCID: https://orcid.org/0000-0003-3697-9612)
- Pinhua Li (ORCID: https://orcid.org/0000-0002-8528-8087)
- Luan-Ting Wu
- Ze Zhang (ORCID: https://orcid.org/0000-0001-9763-4592)
- Peng Xu (ORCID: https://orcid.org/0000-0002-0078-7742)
- Lei Wang (ORCID: https://orcid.org/0000-0001-6580-7671)
- Siqi Chen (ORCID: https://orcid.org/0000-0002-9498-3823)
- Mingjun Li (ORCID: https://orcid.org/0000-0002-9197-3304)
- Qinghai Li (ORCID: https://orcid.org/0000-0002-5300-9629)
- Lin Zhou (ORCID: https://orcid.org/0000-0003-4032-9356)
Institutions
- China Tobacco (CN)
- Anhui Polytechnic University (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-01-27
- DOI
- https://doi.org/10.1021/acs.joc.4c02904
- Primary Topic
- Synthesis of heterocyclic compounds
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Natural Science Foundation of Anhui Province