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Quinoxaline

From Wikipedia, the free encyclopedia
Quinoxaline
Skeletal formula of quinoxaline
Skeletal formula of quinoxaline
Quinoxaline molecule
C=black, H=white, N=blue
Quinoxaline molecule
C=black, H=white, N=blue
Names
Preferred IUPAC name
Quinoxaline[1]
Other names
Benzo[b]pyrazine, Benzopyrazine, Benzoparadiazine, 1,4-Benzodiazine, Phenopiazine, Phenpiazine, Quinazine, Chinoxalin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.001.862Edit this at Wikidata
EC Number
  • 202-047-4
KEGG
UNII
  • InChI=1S/C8H6N2/c1-2-4-8-7(3-1)9-5-6-10-8/h1-6H checkY
    Key: XSCHRSMBECNVNS-UHFFFAOYSA-N checkY
  • InChI=1/C8H6N2/c1-2-4-8-7(3-1)9-5-6-10-8/h1-6H
    Key: XSCHRSMBECNVNS-UHFFFAOYAS
  • c1cccc2nccnc12
Properties
C8H6N2
Molar mass130.150 g·mol−1
Melting point29-32 °C
Boiling point220 to 223 °C (428 to 433 °F; 493 to 496 K)
Acidity (pKa)0.60[2]
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315,H319,H335
P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P321,P332+P313,P337+P313,P362,P403+P233,P405,P501
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

Aquinoxaline, also called abenzopyrazine, inorganic chemistry, is aheterocyclic compound containing a ring complex made up of abenzene ring and apyrazine ring. It isisomeric with othernaphthyridines includingquinazoline,phthalazine andcinnoline.[3] It is a colorless oil that melts just above room temperature. Although quinoxaline itself is mainly of academic interest, quinoxaline derivatives are used as dyes, pharmaceuticals (such asvarenicline), and antibiotics such asolaquindox,carbadox,echinomycin,levomycin andactinoleutin.

Synthesis

[edit]

They can be formed bycondensingortho-diamines with 1,2-diketones. The parent substance of the group, quinoxaline, results whenglyoxal is condensed with1,2-diaminobenzene.[4] Substituted derivatives arise when α-ketonicacids, α-chlorketones, α-aldehydealcohols and α-ketone alcohols are used in place of diketones.[3] Quinoxaline and its analogues may also be formed by reduction of amino acids substituted 1,5-difluoro-2,4-dinitrobenzene (DFDNB):[5]

One study[6] used2-iodoxybenzoic acid (IBX) as acatalyst in the reaction ofbenzil with 1,2-diaminobenzene:

Quinoxaline Synthesis
Quinoxaline Synthesis

Uses

[edit]

Theantitumoral properties of quinoxaline compounds have been of interest.[7] Recently, quinoxaline and its analogs have been investigated as ligands.[8]

References

[edit]
  1. ^International Union of Pure and Applied Chemistry (2014).Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013.The Royal Society of Chemistry. p. 212.doi:10.1039/9781849733069.ISBN 978-0-85404-182-4.
  2. ^Brown, H.C.; et al. (1955). Baude, E.A.; Nachod, F.C. (eds.).Determination of Organic Structures by Physical Methods. New York: Academic Press.
  3. ^ab One or more of the preceding sentences incorporates text from a publication now in thepublic domain: Chisholm, Hugh, ed. (1911). "Quinoxalines".Encyclopædia Britannica. Vol. 22 (11th ed.). Cambridge University Press. p. 760.
  4. ^2,3-Pyrazinedicarboxylic Acid" Reuben G. Jones and Keith C. McLaughlin Org. Synth. 1950, 30, 86.doi:10.15227/orgsyn.030.0086. This paper describes the preparation of quinoxaline as an intermediate.
  5. ^Xiang-Hong Wu; Gang Liu; et al. (2004). "Solution-phase reductive cyclization of 2-quinoxalinol analogs: Systematic study of parallel synthesis".Mol. Divers.8 (2):165–174.doi:10.1023/B:MODI.0000025639.89179.60.PMID 15209169.S2CID 28252647.
  6. ^Heravi, Majid M. (2006)."Facile synthesis of quinoxaline derivatives using o-iodoxybenzoic acid (IBX) at room temperature".Arkivoc.2006 (16):16–22.doi:10.3998/ark.5550190.0007.g02.hdl:2027/spo.5550190.0007.g02.
  7. ^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.
  8. ^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.
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