Benzothiazine
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| Names | |||
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| IUPAC name
2H-1,4-benzothiazine | |||
| Other names
1,4-benzothiazine | |||
| Identifiers | |||
| 3D model (Jmol) | 2H-isomer: Interactive image 4H-isomer: Interactive image | ||
| ChemSpider | 2345079 2H-isomer  11484476 4H-isomer | ||
| PubChem | 3088997 2H-isomer 12805862 4H-isomer | ||
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| 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
- Phenothiazine has an additional benzene ring
- Benzothiazole is another heterocycle containing nitrogen and sulfur
References
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 Hetereocyclic 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.