Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 5
172
Views
3
CrossRef citations to date
0
Altmetric
Original Articles

One-Pot New Synthetic Method for 3-Amino-2-quinoxalinecarbonitrile

, &
Pages 739-743 | Received 11 Oct 2008, Published online: 04 Feb 2010

REFERENCES

  • Kotovskaya , S. K. ; Charushin , V. N. ; Perova , N. M. ; Kodess , M. I. ; Chupakhin , O. N. Intramolecular nucleophilic substitution of hydrogen in (quinoxalinyl-2)aminovinyl derivatives as a new approach to pyrrolo- and indolo[2,3-b]quinoxalines . Synth. Commun. 2004 , 34 , 2531 – 2537 .
  • Monge , A. ; Palop , J. A. ; Urbasos , I. ; Fernandez-Alvarez , E. New quinoxaline and pyrimido[4,5-b]quinoxaline derivatives: Potential antihypertensive and blood platlet antiaggregating agents. J. Heterocycl. Chem. 1989, 26, 1623–1626.
  • Urquiola , C. ; Vieites , M. ; Aguirre , G. , Marın , A. ; Solano , B. ; Arrambide , G. ; Noblia , P. ; Lavaggi , M. L. ; Torre , M. H. ; Gonzalez , M. ; Monge , A. ; Gambino , D. ; Cerecetto , H. Improving anti-trypanosomal activity of 3-aminoquinoxaline-2-carbonitrile N 1,N 4-dioxide derivatives by complexation with vanadium . Bioorg. Med. Chem. 2006 , 14 , 5503 – 5509 .
  • Torre , M. H. ; Gambino , D. ; Araujo , J. ; Cerecetto , H. ; González , M. ; Lavaggi , M. L. ; Azqueta , A. ; López de Cerain , A. ; Monge Vega , A. ; Abram , U. ; Costa-Filho , A. J. Novel Cu(II) quinoxaline N 1,N 4-dioxide complexes as selective hypoxic cytotoxins . Eur. J. Med. Chem. 2005 , 40 , 473 – 480 .
  • Noblia , P. ; Vieites , M. ; Torre , M. H. ; Costa-Filho , A. J. ; Cerecetto , H. ; Gonzalez , M. ; Lavaggi , M. L. ; Adachi , Y. ; Sakurai , H. ; Gambino , D. Novel vanadyl complexes with quinoxaline N1,N4-dioxide derivatives as potent in vitro insulin-mimetic compounds . J. Inorg. Biochem. 2006 , 100 , 281 – 287 .
  • Amin , K. M. ; Ismail , M. M. F. ; Noaman , E. ; Soliman , D. H. ; Ammard , Y. A. New quinoxaline 1,4-di-N-oxides, part 1: Hypoxia-selective cytotoxins and anticancer agents derived from quinoxaline 1,4-di-N-oxides . Bioorg. Med. Chem. 2006 , 14 , 6917 – 6923 .
  • Monge , A. ; Palop , J. A. ; Lopez de Cerain , A. ; Senador , V. ; Martinez , F. J. ; Sainz , Y. ; Narro , S. ; Garcia , E. ; Carlos de Miguel .; Gonzalez , M. ; Hamilton , E. ; Barker , A. J. ; Clarke , E. D. ; Greenhow , D. T. Hypoxia-selective agents derived from quinoxaline 1,4-Di-N-oxides . J. Med. Chem. 1995 , 38 , 1786 – 1792 .
  • Chowdhury , G. ; Kotandeniya , D. ; Daniels , J. S. ; Barnes , C. L. ; Gates , K. S. Enzyme-activated, hypoxia-selective DNA damage by 3-amino-2-quinoxalinecarbonitrile 1,4-di-N-oxide . Chem. Res. Toxicol. 2004 , 17 , 1399 – 1405 .
  • Smith , P. A. S. ; Boyer , J. H. Benzofurazan oxide II: Decomposition of o-nitrophenyl hydrazide . Orga. Synth. Coll. Vol. 1963 , 4 , 74 .
  • Monge , A. ; Palop , J. A. ; Del Castillo , J. C. ; Calderó , J. M. ; Roca , J. ; Romero , G. ; Del Rio , J. ; Lasheras , B. Novel antagonists of 5-HT3 receptors: Synthesis and biological evaluation of piperazinylquinoxaline derivatives . J. Med. Chem. 1993 , 36 , 2745 – 2750 .
  • Begland , R. W. ; Hartter , D. R. Hydrogen cyanide chemistry, IV: Diiminosuccinonitrile reactions with nucleophiles, acyl halides, and carbonyl compounds . J. Org. Chem. 1972 , 37 , 4136 – 4145 .
  • Panayiotis , A. K. ; Charles , W. R. Chemistry of 4-chloro-5-cyano-1,2,3-dithiazoliumchloride . J. Chem. Soc., Perkin Trans. 1 1999 , 111 – 118 .
  • Titov , V. V. ; Kozhokina , L. F. Reactions of 2,2′,3,3′-tetrachloro-6,6-diquinoxalyl with nucleophilic reagents . Chem. Heterocycl. Comp. 1977 , 13 , 337 – 339 .
  • Hermann , K. ; Simchen , G. Synthese cyan-substituierter heterocyclen mit tetraethyl-ammoniumcyanid . Liebigs Ann. Chem. 1981 , 333 – 341 .
  • Ferris , J. P. ; Orgel , L. E. The reactions of bromomalorronitrile with bases . J. Org. Chem. 1965 , 30 , 2365 – 2367 .
  • Pearson , R. G. ; Dillon , R. L. Rates of ionization of pseudo acids IV: Relation between rates and equilibria . J. Am. Chem. Soc. 1953 , 75 , 2439 – 2443 .
  • Hart , H. ; Kim , Y. C. A new synthesis of tetracyanocyclopropanes . J. Org. Chem. 1966 , 31 , 2784 – 2789 .
  • Hart , H. ; Freeman , F. The synthesis and NMR spectra of some tetracyanocyclopropanes . J. Org. Chem. 1963 , 28 , 1220 – 1222 .
  • Brown , D. J. The Chemistry of Heterocyclic Compounds: Quinoxalines Supplement II ; John Wiley & Sons : Hoboken, New Jersey , 2004 ; pp. 367 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.