Oxidant/Solvent-Controlled I₂-Catalyzed Domino Annulation for Selective Synthesis of 2-Aroylbenzothiazoles and 2-Arylbenzothiazoles under Metal-Free Conditions

Renchao Ma, Yuxin Ding, Rener Chen, Zhiming Wang, Lei Wang and Yongmin Ma*

*Institute of Advanced Studies and School of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou 318000, P R China, Email: yongmin.matzc.edu.cn

R. Ma, Y. Ding, R. Chen, Z. Wang, L. Wang, Y. Ma, J. Org. Chem., 2021, 86, 310-321.

DOI: 10.1021/acs.joc.0c02095

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Abstract

Iodine catalyzes simple and practical syntheses of 2-aroylbenzothiazoles and 2-arylbenzothiazoles from 2-aminobenzenethiols and acetophenones under metal-free conditions. Reactions in DMSO as oxidant and reaction medium provide 2-aroylbenzothiazoles, whereas the use of nitrobenzene as oxidant in dioxane as solvent enables the synthesis of 2-arylbenzothiazoles.

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proposed reaction mechanisms

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Key Words

benzothiazoles, DMSO, nitrobenzene

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ID: J42-Y2021