Citation: Yu Lei, Wenjing Zhu, Yajuan Zhang, Qiong Hu, Jie Dong, Yimin Hu. Benzisoxazole core and benzoxazolopyrrolidine via HDDA-derived benzyne with PTIO/DMPO[J]. Chinese Chemical Letters, ;2023, 34(4): 107778. doi: 10.1016/j.cclet.2022.107778 shu

Benzisoxazole core and benzoxazolopyrrolidine via HDDA-derived benzyne with PTIO/DMPO

Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials, State Laboratory Cultivation Base, College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241002, China

yiminhu@ahnu.edu.cn

yiminhu@aliyun.com

Received Date: 16 May 2022
Revised Date: 19 August 2022
Accepted Date: 23 August 2022
Available Online: 25 August 2022

Figures(6)

A novel method for HDDA-derived benzyne trapped by nitrone was developed. This research described a simple and efficient pathway for the synthesis of benzisoxazoles from arynes and PTIO (2-phenyl-4, 4, 5, 5-tetramethylimidazoline-3-oxide-1-oxyl), C−C and C−O bonds were formed in a single step without catalyst under mild conditions. The unexpected cleavage of C−N bond contributed to the formation of isoxazole ring, as indicated by DFT studies. Furthermore, we obtained the structure of benzoxazolopyrrolidine when the trapping agent is DMPO (5, 5-dimethyl-1-pyrroline N-oxide).
- Benzisoxazole,
- HDDA reaction,
- Benzyne,
- Nitrone,
- Heterocycle
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