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Quinoxaline
Quinoxaline numbering.png
IUPAC name
Other names Benzo[a]pyrazine, Benzopyrazine, Benzoparadiazine, 1,4-Benzodiazine, Phenopiazine, Phenpiazine, Quinazine, Chinoxalin
Identifiers
CAS number 91-19-0 Yes check.svgY
PubChem 7045
SMILES
Properties
Molecular formula C8H6N2
Molar mass 130.15 g/mol
 Yes check.svgY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

A quinoxaline, also called a benzopyrazine, in organic chemistry, is a heterocyclic compound containing a ring complex made up of a benzene ring and a pyrazine ring. They are isomeric with quinazolines.

Quinoxalines are used as dyes, pharmaceuticals and antibiotics such as echinomycin, levomycin and actinoleutin.

Some studies were carried out in order to explore the antitumoral properties of quinoxaline compounds:[1]

They can be formed by condensing ortho-diamines with 1,2-diketones. The parent substance of the group, quinoxaline, results when glyoxal is condensed with 1,2-diaminobenzene. Substituted derivatives arise when α-ketonic acids, α-chlorketones, α-aldehyde alcohols and α-ketone alcohols are used in place of diketones.

One study used 2-iodoxybenzoic acid (IBX) as a catalyst in the reaction of benzil with 1,2-diaminobenzene:[2]

Quinoxaline Synthesis

References

  1. ^ "Heterocyclic quinones.2.Quinoxaline-5,6-(and 5-8)-diones-Potential antitumoral agents". Jean Renault, Michel Baron, Patrick Mailliet & al., Eur. J. Med. Chem., 16, 6, 545-550, 1981
  2. ^ Facile synthesis of quinoxaline derivatives using o-iodoxybenzoic acid (IBX) at room temperature (06-2190LP) Majid M. Heravi, Khadijeh Bakhtiari, Maryam H. Tehrani, Negar M. Javadi, and Hossien A. Oskooie ARKIVOC 2006 (xvi) 16-22 provisional link

See also

This article incorporates text from the Encyclopædia Britannica, Eleventh Edition, a publication now in the public domain.

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