Synthesis of <i>2H‐</i>1,2‐Oxazin‐3<i>(6H)</i>‐One via the Cycloaddition of Nitrosobenzene with <i>Gem‐</i>Difluoro‐1,3‐Diene
An efficient method for the synthesis of 2H ‐1,2‐oxazin‐3( 6H )‐one via the nitroso‐Diels‐Alder reaction of nitrosobenzene with gem ‐difluoro‐1,3‐dienes is developed under mild conditions. This strategy features good functional group tolerance, good to high yields, and free of catalyst. The de‐aromatization of heterocyclic gem ‐difluoroalkenes is successfully achieved by this method. The product can be converted into β ‐lactams through base‐promoted rearrangement.
Authors
- Jun O. Liu (ORCID: https://orcid.org/0000-0003-3842-9841)
- Ting Luo (ORCID: https://orcid.org/0000-0002-2107-4282)
- Jian Xu (ORCID: https://orcid.org/0000-0002-9370-4829)
- Gang Zhao (ORCID: https://orcid.org/0000-0002-0162-7783)
Institutions
- University of Science and Technology of China (CN)
- Chinese Academy of Sciences (CN)
- Shanghai Advanced Research Institute (CN)
- Shanghai Institute of Organic Chemistry (CN)
Publication Details
- Journal
- European Journal of Organic Chemistry
- Published
- 2025-04-30
- DOI
- https://doi.org/10.1002/ejoc.202500289
- Primary Topic
- Synthesis and Reactions of Organic Compounds
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Chinese Academy of Sciences
- National Key Research and Development Program of China