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Synthesis 2008(8): 1297-1305
DOI: 10.1055/s-2008-1067008
DOI: 10.1055/s-2008-1067008
PAPER
© Georg Thieme Verlag Stuttgart · New York
Unexpected Formation of Benzothiazoles in the Synthesis of New Heterocycles: Benzo-1,2,4-dithiazines
Weitere Informationen
Received
28 November 2007
Publikationsdatum:
10. April 2008 (online)
Publikationsverlauf
Publikationsdatum:
10. April 2008 (online)
![](https://www.thieme-connect.de/media/synthesis/200808/lookinside/thumbnails/10.1055-s-2008-1067008-1.jpg)
Abstract
The synthesis of benzo-1,2,4-dithiazines was investigated presuming a reversible sulfur-sulfur bond formation. 2-Aminothiophenol, when allowed to react with isothiocyanates, provided benzothiazoles. 2,2′-Diaminodiphenyl disulfide underwent cyclizations very readily without any reducing agent to give, according to the reaction conditions, benzothiazoles or benzo-1,2,4-dithiazines. The developed procedure offers a simple and convenient way to prepare the title compounds in very good to excellent yields. Until now, benzo-1,2,4-dithiazines as well as 2,2′-diaminodiphenyl disulfides bearing aminocarbonothioyl groups were unknown.
Key words
benzo-1,2,4-dithiazines - benzothiazoles - cyclizations - heterocycles - sulfur
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