Issue 75, 2016
From the journal:

Chemical Communications

Thiazolobenzyne: a versatile intermediate for multisubstituted benzothiazoles†

Suguru Yoshida,a   Takahisa Yano,a   Yoshitake Nishiyama,a   Yoshihiro Misawa,a   Masakazu Kondo,b   Takeshi Matsushita,b   Kazunobu Igawa,c   Katsuhiko Tomookac  and  Takamitsu Hosoya*a  

* Corresponding authors

a Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan
E-mail: thosoya.cb@tmd.ac.jp

b Ichihara Research Center, JNC Petrochemical Corporation, 5-1 Goikaigan, Ichihara, Chiba 290-8551, Japan

c Institute for Materials Chemistry and Engineering, Kyushu University, 6-1 Kasuga-koen, Kasuga, Fukuoka 816-8580, Japan

Abstract

Thiazolobenzyne, which is a benzyne species fused with a thiazole ring, was efficiently generated via an iodine–magnesium exchange reaction of an ortho-iodoaryl triflate-type precursor using a trimethylsilylmethyl Grignard reagent as an activator. A wide range of arynophiles reacted efficiently with the thiazolobenzynes generated by this method to afford various multisubstituted benzothiazoles.

Graphical abstract: Thiazolobenzyne: a versatile intermediate for multisubstituted benzothiazoles

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Article information

DOI
https://doi.org/10.1039/C6CC05112J
Article type
Communication
Submitted
18 Jun 2016
Accepted
16 Aug 2016
First published
18 Aug 2016

Chem. Commun., 2016,52, 11199-11202

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Thiazolobenzyne: a versatile intermediate for multisubstituted benzothiazoles

S. Yoshida, T. Yano, Y. Nishiyama, Y. Misawa, M. Kondo, T. Matsushita, K. Igawa, K. Tomooka and T. Hosoya, Chem. Commun., 2016, 52, 11199 DOI: 10.1039/C6CC05112J

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