Thiazine dyes
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Thiazine is an
organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. T ...
containing a ring of four
carbon Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent—its atom making four electrons available to form covalent chemical bonds. It belongs to group 14 of the periodic table. Carbon mak ...
, one
nitrogen Nitrogen is the chemical element with the symbol N and atomic number 7. Nitrogen is a nonmetal and the lightest member of group 15 of the periodic table, often called the pnictogens. It is a common element in the universe, estimated at se ...
and one sulfur atom. There are three isomers of thiazine, 1,2-thiazine, 1,3-thiazine, and 1,4-thiazine, which differ by the arrangement of the nitrogen and sulfur atoms in the ring. Derivatives of thiazine, often referred to as thiazines, are used for dyes,
tranquilizer A tranquilizer is a drug that is designed for the treatment of anxiety, fear, tension, agitation, and disturbances of the mind, specifically to reduce states of anxiety and tension. Etymology Tranquilizer, as a term, was first used by F.F. Yonk ...
s and insecticides.


Preparation

1,4-thiazine can be prepared from the corresponding dione using
aluminium Aluminium (aluminum in American and Canadian English) is a chemical element with the symbol Al and atomic number 13. Aluminium has a density lower than those of other common metals, at approximately one third that of steel. I ...
powder at high temperature.{{Cite journal, last=Barkenbus, first=Charles, last2=Landis, first2=Phillip S., date=February 1948, title=The Preparation of 1,4-Thiazine, journal=Journal of the American Chemical Society, volume=70, issue=2, pages=684–685, doi=10.1021/ja01182a075, issn=0002-7863


Tautomers

Three
tautomer Tautomers () are structural isomers (constitutional isomers) of chemical compounds that readily interconvert. The chemical reaction interconverting the two is called tautomerization. This conversion commonly results from the relocation of a hyd ...
s of 1,4-thiazine exist as above.


See also

* Methylene blue, contains a related ring with nitrogen and a positively charged sulfur atom *
Phenothiazine Phenothiazine, abbreviated PTZ, is an organic compound that has the formula S(C6H4)2NH and is related to the thiazine-class of heterocyclic compounds. Derivatives of phenothiazine are highly bioactive and have widespread use and rich history. T ...
, a thiazine fused with two benzene rings * Thiomorpholine, a saturated analog of thiazine


References