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 ; 4H-isomer: 11484476 ;
PubChem CID	2H-isomer: 3088997; 4H-isomer: 12805862;
UNII	2H-isomer: LP8A4HNV72 ;
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 Key: FBOSKQVOIHEWAX-UHFFFAOYSA-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). verify (what is ?) 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.

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 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.

See also

References