Assembly of N-Heterocyclic Carbenes and Nitroalkenes for Access to Isoxazole Derivatives
A direct isoxazole synthesis employing N-heterocyclic carbenes (NHCs) as single-carbon synthons is reported. Using imidazolium salts as carbon donors, nitroalkenes are transformed into 5-amino-substituted isoxazoles via a nucleophilic addition-cycloaddition-ring opening-hydrolysis cascade reaction. This mild process simultaneously constructs C-O and C-C bonds, accessing products that are difficult to obtain by classical methods. The proposed reaction mechanism is supported by both experimental and computational studies. Several derivatives exhibit broad-spectrum antifungal activity, highlighting their potential as fungicide leads.
Authors
- Zhichao Jin (ORCID: https://orcid.org/0000-0003-3003-6437)
- B. Marambe (ORCID: https://orcid.org/0000-0002-5158-1808)
- Linhong Jin (ORCID: https://orcid.org/0000-0002-2210-3831)
- Ali Dai
- Shengxin Guo
- Ge‐Fei Hao (ORCID: https://orcid.org/0000-0003-4090-8411)
- Barana Chaminda Jayawardana (ORCID: https://orcid.org/0000-0002-8563-2378)
- Zhiguo Zheng
- Jian Wu
Institutions
- University of Peradeniya (LK)
- Nanyang Technological University (SG)
- Guizhou University (CN)
- Shanghai Pesticide Research Institute (CN)
- Institute of Crop Science (JP)
- Renmin University of China (CN)
- Universidad del Noreste (MX)
Publication Details
- Journal
- Organic Letters
- Published
- 2026-04-11
- DOI
- https://doi.org/10.1021/acs.orglett.6c01097
- Primary Topic
- N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- National Natural Science Foundation of China
- Ministry of Education of the People's Republic of China
- Guizhou Science and Technology Department
- Ministry of Finance
- Higher Education Discipline Innovation Project
- Science and Technology Program of Guizhou Province