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

作　　者：Yu Lei Wenjing Zhu Yajuan Zhang Qiong Hu Jie Dong Yimin Hu 

机构地区：[1]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

出　　处：《Chinese Chemical Letters》2023年第4期318-321,共4页中国化学快报（英文版）

基　　金：the National Natural Science Foundation of China (No. 22071001);The Research Culture Funds of Anhui Normal University;Department of Human Resources of Anhui Province for financial support。

摘　　要：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).

关 键 词：Benzisoxazole HDDA reaction BENZYNE NITRONE HETEROCYCLE 

分 类 号：O626[理学—有机化学]