Thiazine

1,2-Thiazin-Isomere:
2H-1,2-Thiazin, 4H-1,2-Thiazin, 6H-1,2-Thiazin
1,3-Thiazin-Isomere:
2H-1,3-Thiazin, 4H-1,3-Thiazin, 6H-1,3-Thiazin
1,4-Thiazin-Isomere:
4H-1,4-Thiazin, 2H-1,4-Thiazin

Thiazine sind heterocyclische organische Verbindungen mit einem Ring aus vier Kohlenstoff-, einem Stickstoff- und einem Schwefel-Atom. Durch die unterschiedliche Anordnung der beiden Heteroatome und der Doppelbindungen ergeben sich insgesamt 8 Isomere.[1] Die meisten Derivate leiten sich vom 1,4-Thiazin ab, es sind aber auch Derivate des 1,2-Thiazin und 1,3-Thiazin bekannt.

Thiazin-Derivate werden bei Farbstoffen, Beruhigungsmitteln und Insektiziden verwendet, wobei die vom 1,4-Thiazin abstammenden Phenothiazine (z. B. Methylenblau als Vertreter der Thiazinfarbstoffe) die häufigsten Derivate darstellen. Wichtige Vertreter der 1,3-Thiazin-Derivate sind zum Beispiel die Cephalosporine, die als Antibiotika zum Einsatz kommen, und das Xylazin.[2] 1,2-Thiazin-Derivate (z. B. partiell hydrierte) erhält man durch [4+2]-Cycloaddition.[3]

Die einfachste Thiazinverbindung ist das 1,4-Thiazin C4H5NS selbst.[4] Im Unterschied dazu enthält die Verbindung Thiomorpholin C4H9NS keine Doppelbindungen im Ring.

Siehe auch

Commons: Thiazines – Sammlung von Bildern, Videos und Audiodateien

Einzelnachweise

  1. ↑ Eintrag zu Thiazine. In: Römpp Online. Georg Thieme Verlag, abgerufen am 22. Mai 2019.
  2. ↑ Arnold Willmes: Taschenbuch Chemische Substanzen: Elemente – Anorganika – Organika – Naturstoffe – Polymere. 3., vollst. überarb. und erw. Auflage. Deutsch, Frankfurt am Main 2007, ISBN 978-3-8171-1787-1.
  3. ↑ Eberhard Breitmaier, Günther Jung: Organische Chemie. Grundlagen, Stoffklassen, Reaktionen, Konzepte, Molekülstruktur. 5., überarb. Auflage. Thieme, Stuttgart/ New York 2005, ISBN 3-13-541505-8.
  4. ↑ C. Barkenbus, P. S. Landis: The Preparation of 1,4-Thiazine. In: J. Am. Chem. Soc. 70, 1948, S. 684–685, doi:10.1021/ja01182a075.

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