Benzothiazine

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Benzothiazine
Skeletal formula of 2H-1,4-benzothiazine
2H-isomer
Skeletal formula of 4H-1,4-benzothiazine
4H-isomer
Space-filling model of the 2H-1,4-benzothiazine molecule
Space-filling model of the 4H-1,4-benzothiazine molecule
Names
IUPAC name
2H-1,4-benzothiazine
Other names
1,4-benzothiazine
Identifiers
3D model (JSmol)
ChemSpider
Properties
C8H7NS
Molar mass 149.21288
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Benzothiazine is a heterocyclic compound consisting of a benzene ring attached to the 6-membered heterocycle thiazine. The name is applied to both the 2H- and 4H-isomers of the molecule.

2,1-Benzothiazine, a type of benzothiazines was first reported in the 1960s. Subsequently, their preparation and intensive biological and physiological studies have been reported. In recent years, 2,1-benzothiazines have been of enormous interest to synthetic chemists. An enantioselective synthesis of such benzothiazines has been developed by Harmata and Hong who have formulated transformations of these compounds designed to target chiral, non-racemic building blocks as well as natural products.

See also[edit]

References[edit]

1. Sulfostyril (2,1-benzothiazine 2,2-dioxide). I. Preparation and reactions of 3,4-dihydrosulfostyril. Loev,B.; Kormendy, M.F. J. Org. Chem. 1965, 30, 3163.

2. Recent Progress in the Chemistry of 2,1-Benzothiazines. Hong, X.; Harmata, M. Progress in Heterocyclic Chemistry, Chapter 1, G. W. Gribble and J. A. Joule, eds, Pergamon Press, Vol 19, pp 1-43 (2008)

3. The Intramolecular, Stereoselective Addition of Sulfoximine Carbanions to α, β-Unsaturated Esters. Harmata, M.; Hong, X. Journal of the American Chemical Society, 2003, 125(19), 5754-5756.

4. Benzothiazines in Synthesis. A Total Synthesis of Pseudopteroxazole. Harmata, M.; Hong, X. Organic Letters, 2005, 7(16), 3581-3583.