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Synthesis 2010(17): 2943-2948
DOI: 10.1055/s-0030-1258155
DOI: 10.1055/s-0030-1258155
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
A Convenient Synthesis of 1,4-Benzothiazepines from 1,3-Benzothiazines via the Ring Transformation of β-Lactam-Condensed 1,3-Benzothiazine Derivatives
Weitere Informationen
Received
30 March 2010
Publikationsdatum:
07. Juli 2010 (online)
Publikationsverlauf
Publikationsdatum:
07. Juli 2010 (online)
![](https://www.thieme-connect.de/media/synthesis/201017/lookinside/thumbnails/10.1055-s-0030-1258155-1.jpg)
Abstract
A convenient synthesis was devised for rare 2,3-disubstituted 4,5-dihydro-1,4-benzothiazepines from 2-aryl-4H-1,3-benzothiazines. The Staudinger reaction of 1,3-benzothiazines obtained with chloroacetyl chloride selectively furnished trans-monochloro-β-lactam-condensed thiazines. The ring expansion of azeto[2,1-b][1,3]benzothiazin-1-one derivatives with sodium methoxide afforded 1,4-benzothiazepines as the sole product in good yields. The structures of the new molecules were proved by means NMR and IR spectroscopy.
Key words
1,4-benzothiazepine - 1,3-benzothiazine - β-lactams - ring expansion - S,N-heterocycles
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