Quinoxaline

Quinoxaline
C=black, H=white, N=blue	C=black, H=white, N=blue
Names
	IUPAC name Quinoxaline
	Other names Benzo[a]pyrazine, Benzopyrazine, Benzoparadiazine, 1,4-Benzodiazine, Phenopiazine, Phenpiazine, Quinazine, Chinoxalin
Identifiers
CAS Number	91-19-0 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:36616 ;
ChEMBL	ChEMBL39444 ;
ChemSpider	21106470 ;
ECHA InfoCard	100.001.862
KEGG	C18575 ;
PubChem CID	7045;
CompTox Dashboard (EPA)	DTXSID6049432 ;
	InChI InChI=1S/C8H6N2/c1-2-4-8-7(3-1)9-5-6-10-8/h1-6H Key: XSCHRSMBECNVNS-UHFFFAOYSA-N ; InChI=1/C8H6N2/c1-2-4-8-7(3-1)9-5-6-10-8/h1-6H Key: XSCHRSMBECNVNS-UHFFFAOYAS;
	SMILES c1cccc2nccnc12;
Properties
Chemical formula	C8H6N2
Molar mass	130.150 g·mol−1
Acidity (pKa)	0.60
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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]

References

^ 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. {{cite book}}: Explicit use of et al. in: |author= (help)CS1 maint: multiple names: editors list (link)
^ 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. {{cite journal}}: Explicit use of et al. in: |author= (help)CS1 maint: multiple names: authors list (link)
^ 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.
^ 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. {{cite journal}}: Explicit use of et al. in: |author= (help)
^ 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.

This article incorporates text from a publication now in the public domain: Chisholm, Hugh, ed. (1911). Encyclopædia Britannica (11th ed.). Cambridge University Press. {{cite encyclopedia}}: Missing or empty |title= (help)

[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. {{cite book}}: Explicit use of et al. in: |author= (help)CS1 maint: multiple names: editors list (link)

[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. {{cite journal}}: Explicit use of et al. in: |author= (help)CS1 maint: multiple names: authors list (link)

[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. {{cite journal}}: Explicit use of et al. in: |author= (help)

[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.

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