Synthesis 2020; 52(20): 3058-3064
DOI: 10.1055/s-0040-1707204
paper
© Georg Thieme Verlag Stuttgart · New York

Iodine- and TBHP-Promoted Acylation of Benzothiazoles under Metal-Free Conditions

Bin Wang
,
Qianwei Zhang
,
Zhongqi Guo
,
College of Chemistry, Xinjiang University, Urumqi 830046, P. R. of China   eMail: [email protected]   eMail: [email protected]
› Institutsangaben
This work was supported by the National Science Foundation of China (Grant Nos. 21961038 and 21462041).
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Publikationsverlauf

Received: 14. Juni 2020

Accepted after revision: 16. Juni 2020

Publikationsdatum:
23. Juli 2020 (online)


Abstract

A simple protocol for the synthesis of 2-acylbenzothiazoles using aryl ketones and benzothiazoles in the presence of I2 and TBHP is described. Acylation of the benzothiazoles is achieved through a sequence involving oxidation of the aryl ketone to an aryl glyoxal, ring-opening of the benzothiazole followed by condensation of the amino group with the aryl glyoxal, cyclization and oxidation. The method avoids the use of metals and toxic solvents. In addition, this protocol has the advantage of broad scope and provides good to excellent product yields.

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