Benzothiazine

Benzothiazine

2H-isomer 4H-isomer
Names
IUPAC name 2H-1,4-benzothiazine
Other names 1,4-benzothiazine
Identifiers
CAS Number	2H-isomer: 255-17-4 4H-isomer: 255-16-3
3D model (JSmol)	2H-isomer: Interactive image 4H-isomer: Interactive image
ChemSpider	2H-isomer: 2345079  N 4H-isomer: 11484476  N
PubChem CID	2H-isomer: 3088997 4H-isomer: 12805862
UNII	2H-isomer: LP8A4HNV72  Y
CompTox Dashboard (EPA)	2H-isomer: DTXSID70180186
InChI InChI=1S/C8H7NS/c1-2-4-8-7(3-1)9-5-6-10-8/h1-5H,6H2 N Key: FBOSKQVOIHEWAX-UHFFFAOYSA-N N 4H-isomer:InChI=1S/C8H7NS/c1-2-4-8-7(3-1)9-5-6-10-8/h1-6,9H Key: ZLILRRGWBOKBIG-UHFFFAOYSA-N
SMILES 2H-isomer:N=1c2c(SCC=1)cccc2 4H-isomer:c1ccc2S/C=C\Nc2c1
Properties
Chemical formula	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). N  verify  (what is  YN ?) 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

Further reading

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