Thiazines

from Wikipedia, the free encyclopedia
1,2-thiazine isomers:
2 H -1,2-thiazine, 4 H -1,2-thiazine, 6 H -1,2-thiazine
1,3-thiazine isomers:
2 H -1,3-thiazine, 4 H -1,3-thiazine, 6 H -1,3-thiazine
1,4-thiazine isomers:
4 H -1,4-thiazine, 1 H -1,4-thiazine

Thiazines are heterocyclic organic compounds having a ring of four carbon -, a nitrogen - and a sulfur - atom . The different arrangement of the two heteroatoms and the double bonds results in a total of 8 isomers . Most derivatives are derived from 1,4-thiazine , but derivatives of 1,2-thiazine and 1,3-thiazine are also known.

Thiazine derivatives are used in dyes , sedatives and insecticides , the phenothiazines derived from 1,4-thiazine (e.g. methylene blue as a representative of thiazine dyes) being the most common derivatives. Important representatives of the 1,3-thiazine derivatives are, for example, the cephalosporins , which are used as antibiotics , and xylazine . 1,2-thiazine derivatives (e.g. partially hydrogenated) are obtained by [4 + 2] cycloaddition .

The simplest thiazine compound is the 1,4-thiazine C 4 H 5 NS itself. In contrast, the compound thiomorpholine C 4 H 9 NS does not contain any double bonds in the ring.

See also

Web links

Commons : Thiazines  - collection of images, videos and audio files

Individual evidence

  1. ↑ Entry on thiazines. In: Römpp Online . Georg Thieme Verlag, accessed on May 22, 2019.
  2. ↑ Arnold Willmes: Taschenbuch Chemical Substances: Elements - Inorganics - Organics - Natural Products - Polymers. 3rd, completely revised and exp. Edition. German, Frankfurt am Main 2007, ISBN 978-3-8171-1787-1 .
  3. ↑ Eberhard Breitmaier, Günther Jung: Organic chemistry. Basics, substance classes, reactions, concepts, molecular structure. 5th, revised. Edition. Thieme, Stuttgart / New York 2005, ISBN 3-13-541505-8 .
  4. ↑ C. Barkenbus, PS Landis: The Preparation of 1,4-thiazines. In: J. Am. Chem. Soc. 70, 1948, pp. 684-685, doi: 10.1021 / ja01182a075 .