Issue 10, 2015
From the journal:

Organic & Biomolecular Chemistry

Copper-catalyzed ring expansion of 2-aminobenzothiazoles with alkynyl carboxylic acids to 1,4-benzothiazines†

Jing-Wen Qiu,a   Bo-Lun Hu,a   Xing-Guo Zhang,*a   Ri-Yuan Tang,a   Ping Zhonga  and  Jin-Heng Li*b  

* Corresponding authors

a College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, China
E-mail: zxg@wzu.edu.cn

b State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China
E-mail: jhli@hnu.edu.cn

Abstract

A new ring expansion of 2-aminobenzothiazoles with alkynyl carboxylic acids was developed, which allows for one-pot synthesis of 1,4-benzothiazines in moderate to excellent yields. The cascade reaction was achieved through decarboxylative coupling, nucleophilic ring-opening reaction and intramolecular hydroamination process.

Graphical abstract: Copper-catalyzed ring expansion of 2-aminobenzothiazoles with alkynyl carboxylic acids to 1,4-benzothiazines

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Article information

DOI
https://doi.org/10.1039/C4OB02467B
Article type
Paper
Submitted
24 Nov 2014
Accepted
20 Jan 2015
First published
20 Jan 2015

Org. Biomol. Chem., 2015,13, 3122-3127

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Copper-catalyzed ring expansion of 2-aminobenzothiazoles with alkynyl carboxylic acids to 1,4-benzothiazines

J. Qiu, B. Hu, X. Zhang, R. Tang, P. Zhong and J. Li, Org. Biomol. Chem., 2015, 13, 3122 DOI: 10.1039/C4OB02467B

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