Ionic Reactivity of 2-Isocyanoaryl Thioethers: Access to 2-Halo and 2-Aminobenzothia/Selenazoles

Jinhuan Dong, Junlin Hu, Xiaoli Liu, Shaoguang Sun*, Lan Bao, Mengying Jia* and Xianxiu Xu*

*Panzhihua University, Panzhihua, Sichuan 617000; Shandong Normal University, Jinan 250014, China, Email: timsunpzhu.edu.cn, jiamy231sdnu.edu.cn, xuxx677sdnu.edu.cn

J. Dong, J. Hu, X. Liu, S. Sun, L. Bao, M. Jia, X. Xu, J. Org. Chem., 2022, 87, 2845-2852.

DOI: 10.1021/acs.joc.1c02747

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Abstract

An ionic cascade insertion/cyclization reaction of thia-/selena-functionalized arylisocyanides enables an efficient and practical synthesis of 2-halobenzothiazole/benzoselenazole derivatives. Additionally, a facile access to 2-aminobenzothiazoles is also achieved by the one-pot cascade reaction of 2-isocyanoaryl thioethers, iodine, and amines.

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proposed mechanism

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Key Words

benzothiazoles, iodine

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ID: J42-Y2022