Quinoxaline

Quinoxaline
Quinoxaline
Identifiers
CAS number 91-19-0 YesY
PubChem 7045
ChemSpider 21106470 YesY
KEGG C18575 YesY
ChEBI CHEBI:36616 N
ChEMBL CHEMBL39444 YesY
Jmol-3D images Image 1
Properties
Molecular formula C8H6N2
Molar mass 130.15 g/mol
Acidity (pKa) 0.60[1]
 N (verify) (what is: YesY/N?)
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. It is isomeric with 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, quinoxalie and its analogues 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

  1. ^ Brown, H.C., et al., in Baude, E.A. and Nachod, F.C., Determination of Organic Structures by Physical Methods, Academic Press, New York, 1955.
  2. ^ 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
  3. ^ Regioselective Synthesis of Asymmetrically Substituted 2-Quinoxalinol Salen Ligands. Xianghong Wu, Anne E. V. Gorden. J. Org. Chem., 72, 8691-8699, 2007
  4. ^ Solution-phase reductive cyclization of 2-quinoxalinol analogs: Systematic study of parallel synthesis. Xiang-Hong Wu, Gang Liu, etal., Mol. Diver., 8, 165-147, 2004
  5. ^ 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 a publication now in the public domainChisholm, Hugh, ed (1911). Encyclopædia Britannica (11th ed.). Cambridge University Press. 


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Look at other dictionaries:

  • Quinoxaline — Quin*ox a*line, n. [Quinoline + glyoxal.] (Chem.) Any one of a series of complex nitrogenous bases obtained by the union of certain aniline derivatives with glyoxal or with certain ketones. [Written also {chinoxaline}.] [1913 Webster] …   The Collaborative International Dictionary of English

  • quinoxaline — ● quinoxaline nom féminin Dérivé bicyclique de la pyrazine, dont le squelette se retrouve dans la riboflavine. Nom générique des dérivés de ce composé …   Encyclopédie Universelle

  • quinoxaline — qui·nox·a·line kwi näk sə .lēn, .līn n a weakly basic bicyclic compound C8H6N2 made by condensing the ortho form of phenylenediamine with glyoxal and having fused benzene and pyrazine rings also any of various derivatives of quinoxaline having… …   Medical dictionary

  • quinoxaline — /kwi nok seuh leen , lin/, n. Chem. a colorless, crystalline, water soluble powder, C8H6N2, used chiefly in organic synthesis. Also, quinoxalin /kwi nok seuh lin/. [1880 85; QUIN(INE) + (GLY)OXAL + INE2] * * * …   Universalium

  • quinoxaline — noun A bicyclic heterocycle consisting of a benzene ring fused to that of pyrazine Syn: benzopyrazine …   Wiktionary

  • quinoxaline — qui·nox·a·line …   English syllables

  • quinoxaline — /kwɪnˈɒksəlin/ (say kwin oksuhleen) noun 1. a bicyclic heterocyclic amine, C8H6N2. 2. any of a class of compounds based on this structure. {German chinoxalin, from chin(oline) quinoline + (gly)oxal + in ine2} …  

  • quinoxaline — …   Useful english dictionary

  • chinoxaline — Quinoxaline Quin*ox a*line, n. [Quinoline + glyoxal.] (Chem.) Any one of a series of complex nitrogenous bases obtained by the union of certain aniline derivatives with glyoxal or with certain ketones. [Written also {chinoxaline}.] [1913 Webster] …   The Collaborative International Dictionary of English

  • NBQX — IUPAC name 2,3 Dioxo 6 nitro 1,2,3,4 tetrahydrobenzo[f]quinoxaline 7 sulfonamide …   Wikipedia

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