I2/TBHP-Mediated tandem cyclization and oxidation reaction: Facile access to 2-substituted thiazoles and benzothiazoles

Li Liu; Chen Tan; Rong Fan; Zihan Wang; Hongguang Du; Kun Xu; Jiajing Tan

doi:10.1039/C8OB02826E

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I₂/TBHP-Mediated tandem cyclization and oxidation reaction: Facile access to 2-substituted thiazoles and benzothiazoles†

Li Liu,^a Chen Tan,^a Rong Fan,^a Zihan Wang,^a Hongguang Du,

*^a Kun Xu

*^b and Jiajing Tan

*^a

Author affiliations

* Corresponding authors

^a Department of Organic Chemistry, College of Science, Beijing University of Chemical Technology, Beijing 100029, P. R. China
E-mail: dhg@mail.buct.edu.cn, tanjj@mail.buct.edu.cn

^b College of Chemistry and Pharmaceutical Engineering, Nanyang Normal University, Nanyang, Henan 473061, P. R. China
E-mail: xukun@nynu.edu.cn

Abstract

The efficient synthesis of 2-substituted thiazoles and benzothiazoles has been accomplished employing readily available cysteine esters and 2-aminobenzenethiols as N and S sources. The reaction proceeds under an I₂/TBHP system and involves a one-pot tandem cyclization and oxidation sequence. A diverse range of aldehydes is amenable for this transition-metal-free protocol, which provides an alternative method to rapidly access thiazole-containing molecules.

This article is part of the themed collection: Synthetic methodology in OBC

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Article information

DOI: https://doi.org/10.1039/C8OB02826E
Article type: Communication
Submitted: 13 Nov 2018
Accepted: 09 Dec 2018
First published: 10 Dec 2018

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Org. Biomol. Chem., 2019,17, 252-256

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I₂/TBHP-Mediated tandem cyclization and oxidation reaction: Facile access to 2-substituted thiazoles and benzothiazoles

L. Liu, C. Tan, R. Fan, Z. Wang, H. Du, K. Xu and J. Tan, Org. Biomol. Chem., 2019, 17, 252 DOI: 10.1039/C8OB02826E

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Organic & Biomolecular Chemistry