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Synlett 2008(18): 2882-2884  
DOI: 10.1055/s-0028-1083533
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

The First Synthesis of 2,2′:5′,2′′-Terthiazole

Hiroyuki Kurata*, Hideki Takakuwa, Kouzou Matsumoto, Takeshi Kawase, Masaji Oda
Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043, Japan
Fax: +81(6)68505387; e-Mail: kurata@chem.sci.osaka-u.ac.jp;
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Publication History

Received 17 June 2008
Publication Date:
15 October 2008 (online)

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Abstract

2,2′:5′,2′′-Terthiazole, a previously unknown terthiazole isomer, was prepared by copper-mediated oxidative coupling of 2-lithiothiazole. The yield was improved in the presence of equimolar 2,2′-bithiazole. The 5,5′′-positions were cleanly lithiated by lithium diisopropylamide, which demonstrates its potential in the extension of π-systems.

Key words

thiazole - copper - coupling - lithiation - oligomer

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1

Present address: Department of Materials Science and Chemistry, Graduate School of Engineering, University of Hyogo, 2167 Shosha, Himeji, Hyogo 671-2201, Japan.

12

We also examined this reaction by using 3.0 equivalents of CuCl2, and the yield of 4 was 15%.

14

Oxidation of 7 and the properties of the oxidized species will be reported elsewhere.