Quinoxaline

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Quinoxaline
Skeletal formula of quinoxaline
Quinoxaline molecule Quinoxaline molecule
Identifiers
CAS number 91-19-0 YesY
PubChem 7045
ChemSpider 21106470 YesY
KEGG C18575 YesY
ChEBI CHEBI:36616 YesY
ChEMBL CHEMBL39444 YesY
Jmol-3D images Image 1
Properties
Molecular formula C8H6N2
Molar mass 130.15 g mol−1
Acidity (pKa) 0.60[1]
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
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. It is isomeric with other naphthyridines including quinazoline, phthalazine and cinnoline.

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:[2] Recently, quinoxaline and its analogs have been investigated as the catalyst's ligands:[3]

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. Quinoxaline and its analogues may also be form by reduction of amino acids substituted 1,5-difluoro-2,4-dinitrobenzene (DFDNB):[4]

One study used 2-iodoxybenzoic acid (IBX) as a catalyst in the reaction of benzil with 1,2-diaminobenzene:[5]

Quinoxaline Synthesis

References[edit]

  1. ^ Brown, H.C., et al. (1955). Baude, E.A. and Nachod, F.C., ed. Determination of Organic Structures by Physical Methods. New York: Academic Press. 
  2. ^ Jean Renault, Michel Baron, Patrick Mailliet et al. (1981). "Heterocyclic quinones.2.Quinoxaline-5,6-(and 5-8)-diones-Potential antitumoral agents". Eur. J. Med. Chem. 16 (6): 545–550. 
  3. ^ Xianghong Wu, Anne E. V. Gorden (2007). "Regioselective Synthesis of Asymmetrically Substituted 2-Quinoxalinol Salen Ligands". J. Org. Chem. 72 (23): 8691–8699. doi:10.1021/jo701395w. PMID 17939720. 
  4. ^ Xiang-Hong Wu, Gang Liu, et al. (2004). "Solution-phase reductive cyclization of 2-quinoxalinol analogs: Systematic study of parallel synthesis". Mol. Diver. 8 (2): 165–147. doi:10.1023/B:MODI.0000025639.89179.60. 
  5. ^ Heravi, Majid M. (2006). "Facile synthesis of quinoxaline derivatives using o-iodoxybenzoic acid (IBX) at room temperature". Arkivoc 2006 (16). doi:10.3998/ark.5550190.0007.g02. 

Public Domain This article incorporates text from a publication now in the public domainChisholm, Hugh, ed. (1911). Encyclopædia Britannica (11th ed.). Cambridge University Press.