Oxazines
Encyclopedia
Oxazines are heterocyclic compound
s containing one oxygen
and one nitrogen
.
Many isomer
s 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.
Benzoxazine is a molecule where an oxazine ring a heterocyclic six-membered ring with oxygen and nitrogen atom which is attached to a benzene ring. There are several benzoxazine structures depending on the position of the heteroatoms. The numbering is made in such a way that the oxygen position precedes the nitrogen. Thus, structure c is a 1,4-benzoxazine. This is because the benzoxazine was originally the compound with a double bond, such as in structured. The word, dihydro, indicates the hydrogenated version of benzoxazine.
It is the 1,3-benzoxazines that are the subject of interest for development of polymeric materials as this class of benzoxazines readily polymerizes via cationic ring-opening polymerization. The IUPAC name avoids the reversing of 1,3 into 3,1 from the structure a into. Instead, the position of the oxygen is indicated by [e] for structure and [d] for structure b by alphabetically counting the atoms in the oxazine ring. While the accurate naming must still follow IUPAC notation, it is very complex and impractical for routine use. Thus, a convention has been developed to abbreviate the name of the benzoxazine.
Heterocyclic compound
A heterocyclic compound is a cyclic compound which has atoms of at least two different elements as members of its ring. The counterparts of heterocyclic compounds are homocyclic compounds, the rings of which are made of a single element....
s containing one oxygen
Oxygen
Oxygen is the element with atomic number 8 and represented by the symbol O. Its name derives from the Greek roots ὀξύς and -γενής , because at the time of naming, it was mistakenly thought that all acids required oxygen in their composition...
and one nitrogen
Nitrogen
Nitrogen is a chemical element that has the symbol N, atomic number of 7 and atomic mass 14.00674 u. Elemental nitrogen is a colorless, odorless, tasteless, and mostly inert diatomic gas at standard conditions, constituting 78.08% by volume of Earth's atmosphere...
.
Many isomer
Isomer
In chemistry, isomers are compounds with the same molecular formula but different structural formulas. Isomers do not necessarily share similar properties, unless they also have the same functional groups. There are many different classes of isomers, like stereoisomers, enantiomers, geometrical...
s 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
Ifosfamide
Ifosfamide is a nitrogen mustard alkylating agent used in the treatment of cancer.It is sometimes abbreviated "IFO".-Uses:It is given as a treatment for a variety of cancers, including:...
and morpholine
Morpholine
Morpholine is an organic chemical compound having the chemical formula O2NH. This heterocycle, pictured at right, features both amine and ether functional groups. Because of the amine, morpholine is a base; its conjugate acid is called morpholinium...
(tetrahydro-1,4-oxazine). A commercially available dihydro-1,3-oxazine is a reagent in the Meyers synthesis
Meyers synthesis
The Meyers synthesis is an organic synthesis for the preparation of unsymmetrical aldehydes via hydrolysis of an oxazine . The reaction is named after the American chemist Albert I. Meyers....
for aldehydes. Fluorescent dyes such as Nile red
Nile red
Nile red is a lipophilic stain. It is produced by boiling a solution of Nile blue with sulfuric acid. As can be seen from the structural formulae, this process replaces an amino group with a carbonyl group. Nile red stains intracellular lipid droplets red...
and Nile blue
Nile blue
Nile blue is a stain used in biology and histology. It may be used with live or fixed cells, and imparts a blue colour to cell nuclei....
are based on the aromatic benzophenoxazine.
Benzoxazine is a molecule where an oxazine ring a heterocyclic six-membered ring with oxygen and nitrogen atom which is attached to a benzene ring. There are several benzoxazine structures depending on the position of the heteroatoms. The numbering is made in such a way that the oxygen position precedes the nitrogen. Thus, structure c is a 1,4-benzoxazine. This is because the benzoxazine was originally the compound with a double bond, such as in structured. The word, dihydro, indicates the hydrogenated version of benzoxazine.
It is the 1,3-benzoxazines that are the subject of interest for development of polymeric materials as this class of benzoxazines readily polymerizes via cationic ring-opening polymerization. The IUPAC name avoids the reversing of 1,3 into 3,1 from the structure a into. Instead, the position of the oxygen is indicated by [e] for structure and [d] for structure b by alphabetically counting the atoms in the oxazine ring. While the accurate naming must still follow IUPAC notation, it is very complex and impractical for routine use. Thus, a convention has been developed to abbreviate the name of the benzoxazine.