Quinoxaline

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Quinoxaline
Skeletal formula of quinoxaline
Quinoxaline molecule
Quinoxaline molecule
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 InfoCard 100.001.862 Edit 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 mass 130.150 g·mol−1
Melting point 29-32 °C
Boiling point 220 to 223 °C (428 to 433 °F; 493 to 496 K)
Acidity (pKa) 0.60[2]
Hazards
GHS labelling:
GHS07: Exclamation mark
Signal word
 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 their standard state (at 25 °C [77 °F], 100 kPa).
checkY  (what is checkY☒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.[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, and antibiotics such as , carbadox, echinomycin, and .

Synthesis[]

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.[4] Substituted derivatives arise when α-ketonic acids, α-chlorketones, α-aldehyde alcohols 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]

Quinoxaline Synthesis

Uses[]

The antitumoral properties of quinoxaline compounds have been of interest.[6] Recently, quinoxaline and its analogs have been investigated as the catalyst's ligands.[7]

One study used 2-iodoxybenzoic acid (IBX) as a catalyst in the reaction of benzil with 1,2-diaminobenzene:[8]

Pyrazinamide and Morinamide are made out of quinoxaline. It is also used to make amiloride.

References[]

  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. ^ a b  One or more of the preceding sentences incorporates text from a publication now in the public domain: Chisholm, Hugh, ed. (1911). "Quinoxalines". Encyclopædia Britannica. 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. ^ 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.
  7. ^ 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.
  8. ^ 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.
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