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Metal-Free Synthesis of 2-Aminobenzothiazoles via Aerobic Oxidative Cyclization/Dehydrogenation of Cyclohexanones and Thioureas

Jinwu Zhao, Huawen Huang, Wanqing Wu, Huoji Chen and Huanfeng Jiang*

*School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, P. R. China, Email: jianghfscut.edu.cn

J. Zhao, H. Huang, W. Wu, H. Chen, H. Jiang, Org. Lett., 2013, 15, 2604-2607.

DOI: 10.1021/ol400773k (free Supporting Information)


Abstract

A catalytic amount of iodine enables a metal-free synthesis of 2-aminobenzothiazoles from cyclohexanones and thioureas in the presence of molecular oxygen as the oxidant under mild conditions. Various 2-aminobenzothiazoles, 2-aminonaphtho[2,1-d]thiazoles, and 2-aminonaphtho[1,2-d]thiazoles were prepared in satisfactory yields.

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Key Words

benzothiazoles, oxygen, iodine


ID: J54-Y2013