Benzothiazine

Benzothiazine
IUPAC name 2H-1,4-benzothiazine
Other names 1,4-benzothiazine
Identifiers
	PubChem	3088997 2H- isomer, 12805862 4H- isomer
ChemSpider	2345079 2H-isomer, 11484476 4H-isomer
Jmol-3D images	Image 1 Image 2
SMILES N=1c2c(SCC=1)cccc2 2H-isomer c1ccc2S/C=C\Nc2c1 4H-isomer
InChI InChI=1S/C8H7NS/c1-2-4-8-7(3-1)9-5-6-10-8/h1-5H,6H2 2H-isomer Key: FBOSKQVOIHEWAX-UHFFFAOYSA-N InChI=1/C8H7NS/c1-2-4-8-7(3-1)9-5-6-10-8/h1-5H,6H2 2H-isomer Key: FBOSKQVOIHEWAX-UHFFFAOYAU InChI=1/C8H7NS/c1-2-4-8-7(3-1)9-5-6-10-8/h1-6,9H 4H-isomer Key: ZLILRRGWBOKBIG-UHFFFAOYAC
Properties
Molecular formula	C8H7NS
Molar mass	149.21288
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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- (top) and 4H- (bottom) 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.