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The 8 existing isomers of oxazine[1]

Oxazines are heterocyclic compounds containing one oxygen and one nitrogen atom in a doubly unsaturated six-membered ring. Isomers exist depending on the relative position of the heteroatoms and relative position of the double bonds

By extension, the derivatives are also referred to as oxazines; examples include ifosfamide and morpholine (tetrahydro-1,4-oxazine). A commercially available dihydro-1,3-oxazine is a reagent in the Meyers synthesis for aldehydes. Fluorescent dyes such as Nile red and Nile blue are based on the aromatic benzophenoxazine. Cinnabarine and cinnabaric acid are two naturally occurring dioxazines, being derived from biodegradation of tryptophan.[2]


Dioxazines are pentacyclic compounds consisting of two oxazine subunits. A commercially important example is the pigment pigment violet 23.[3]



  1. ^ Theophil Eicher, Siegfried Hauptmann, Andreas Speicher: The Chemistry of Heterocycles: Structures, Reactions, Synthesis, and Applications, 3rd, Completely Revised and Enlarged Edition, John Wiley & Sons, p. 442 (Oxazines, p. 442, at Google Books).
  2. ^ Stone, Trevor W.; Stoy, Nicholas; Darlington, L. Gail "An expanding range of targets for kynurenine metabolites of tryptophan" Trends in Pharmacological Sciences 2013, volume 34, pp. 136-143.
  3. ^ Chamberlain, Terence "Dioxazine violet pigments" from High Performance Pigments Edited by Smith, Hugh M. 2002,185-194. doi:10.1002/3527600493.ch12

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