Oxazine Dye
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Oxazines are heterocyclic compounds containing one
oxygen Oxygen is the chemical element with the symbol O and atomic number 8. It is a member of the chalcogen group in the periodic table, a highly reactive nonmetal, and an oxidizing agent that readily forms oxides with most elements as ...
and 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 ...
atom in a doubly unsaturated six-membered ring. Isomers exist depending on the relative position of the
heteroatom In chemistry, a heteroatom () is, strictly, any atom that is not carbon or hydrogen. Organic chemistry In practice, the term is usually used more specifically to indicate that non-carbon atoms have replaced carbon in the backbone of the molecula ...
s and relative position of the
double bond In chemistry, a double bond is a covalent bond between two atoms involving four bonding electrons as opposed to two in a single bond. Double bonds occur most commonly between two carbon atoms, for example in alkenes. Many double bonds exist betwee ...
s. By extension, the derivatives are also referred to as oxazines; examples include
ifosfamide Ifosfamide (IFO), sold under the brand name Ifex among others, is a chemotherapy medication used to treat a number of types of cancer. This includes testicular cancer, soft tissue sarcoma, osteosarcoma, bladder cancer, small cell lung cancer, ...
and morpholine (tetrahydro-1,4-oxazine). A commercially available dihydro-1,3-oxazine is a reagent in the Meyers synthesis of 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 Tryptophan (symbol Trp or W) is an α-amino acid that is used in the biosynthesis of proteins. Tryptophan contains an α-amino group, an α-carboxylic acid group, and a side chain indole, making it a polar molecule with a non-polar aromatic ...
.


Dioxazines

Dioxazines are pentacyclic compounds consisting of two oxazine subunits. A commercially important example is the pigment
pigment violet 23 Pigment violet 23 is an organic compound that is a commercial pigment. It is member of the di oxazine family of heterocyclic compounds, but derived from carbazoles. It is prepared by condensation of chloranil and 3-amino-''N''-ethylcarbazole. It ...
.


Benzoxazines

Benzoxazine Benzoxazines are a group of isomeric bicyclic heterocyclic chemical compounds that consist of a benzene ring fused to an oxazine ring. The different isomers depend on the relative positions of the oxygen and nitrogen atoms in the oxazine ring, on ...
s are bicyclic compounds formed by the ring fusion of a benzene ring with an oxazine.
Polybenzoxazine Polybenzoxazines, also called benzoxazine resins, are cured polymerization products derived from benzoxazine monomers. Monomers Benzoxazines are bicyclic heterocyclic compounds containing one oxygen and one nitrogen atom in a doubly unsaturated ...
s are a class of polymers formed by the reaction of phenols, formaldehyde, and primary amines which on heating to ~200 °C (~400 °F) polymerise to produce polybenzoxazine networks. The resulting high molecular weight thermoset polymer matrix composites are used where enhanced mechanical performance, flame and fire resistance compared to epoxy and phenolic resins is required.Handbook of Benzoxazine Resins, ed. Hatsuo Ishida And Tarek Agag, Elsevier B.V., 2011,


Images

File:Morpholine-flat-2D-skeletal.png, Morpholine File:10H-phenoxazine 200.svg,
Phenoxazine Phenoxazine is a heterocyclic compound. The structure of phenoxazine consists of an oxazine fused to two benzene rings. It occurs as the central core of a number of naturally occurring chemical compounds such as dactinomycin and litmus. The dye ...
File:C.I. Pigment Violet 23.svg,
Pigment violet 23 Pigment violet 23 is an organic compound that is a commercial pigment. It is member of the di oxazine family of heterocyclic compounds, but derived from carbazoles. It is prepared by condensation of chloranil and 3-amino-''N''-ethylcarbazole. It ...
is a commercially useful pigment.


References


External links

* {{MeshName, Oxazines
Development of polymeric materials as a class of benzoxazines