Skip to main content
SpringerLink
Log in

Synthesis and Crystal Structure of the Azoxydichinyl Helicene, Pyrido[3,2-f]quinolino[6,5-c]cinnoline 5-Oxide Monohydrate

  • Original Paper
  • Published:
Journal of Chemical Crystallography Aims and scope Submit manuscript

Abstract

The helicene, pyrido[3,2-f]quinolino[6,5-c]cinnoline 5-oxide, was prepared by treatment of 6-hydroxylaminoquinoline with xanthine oxidase or treatment of 6-nitroquinoline with glucose in 30% NaOH and the product characterized using NMR, high resolution mass spectrometry, and X-ray crystallography. The hydrogens on carbons 7 and 12 of the terminal aromatic rings are separated by 2.495 Å creating an angle of 25.0° between the planes of the two quinoline ring systems. In the crystal, water molecules serve to link the helicenes into a one dimensional chain structure forming a hydrogen bonded bridge between N2 of one molecule and N4 of another. The molecule (C18H10N4O·H2O) crystallized in the monoclinic P21/n space group. Unit cell parameters for pyrido[3,2-f]quinolino[6,5-c]cinnoline 5-oxide monohydrate: a = 7.0829(12), b = 18.559(3), c = 11.0985(19) Å, β = 107.736(2)°, and Ζ = 4.

Graphical Abstract

The helicene, pyrido[3,2-f]quinolino[6,5-c]cinnoline 5-oxide, was prepared by treatment of 6-hydroxylaminoquinoline with xanthine oxidase or treatment of 6-nitroquinoline with glucose in 30% NaOH and the product characterized using NMR, high resolution mass spectrometry, and X-ray crystallography on the monohydrate form of the molecule.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. Kotandeniya D, Ganley B, Gates KS (2002) Bioorg Med Chem Lett 12:2325

    Article  CAS  Google Scholar 

  2. Solano B, Junnotula V, Marin A, Villar R, Burguete A, Vicente E, Perez-Silanes S, Monge A, Dutta S, Sarkar U, Gates KS (2007) J Med Chem 50:5485

    Article  CAS  Google Scholar 

  3. Junnotula V, Sarkar U, Sinha S, Gates KS (2009) J Am Chem Soc 131:1015

    Article  CAS  Google Scholar 

  4. Fuchs T, Gates KS, Hwang J-T, Greenberg MM (1999) Chem Res Toxicol 12:1190

    Article  CAS  Google Scholar 

  5. Knueppel CA (1899) Liebigs Ann 310:75

    CAS  Google Scholar 

  6. Huisgen R (1948) Liebigs Ann 559:127

    Google Scholar 

  7. Farrar, W. V. (1965) J Chem Soc 799

  8. Rummens FHA, Bellaart AC (1967) Tetrahedron 23:2735

    Article  CAS  Google Scholar 

  9. Galbraith HW, Degering EF, Hitch EF (1951) J Am Chem Soc 73:1323

    Article  CAS  Google Scholar 

  10. Sheldrick G (2008) Acta Cryst A64:112

    CAS  Google Scholar 

  11. Barbour LJ (2001) J Supramol Chem 1:189

    Article  CAS  Google Scholar 

  12. Bazzini C, Caronna T, Fontana F, Macchi P, Mele A, Sora IN, Panzeri W, Sironi A (2008) New J Chem 32:1710

    Article  CAS  Google Scholar 

  13. Staab HA, Zirnstein MA, Krieger C (1989) Angew Chem Int Ed Eng 28:86

    Article  Google Scholar 

Download references

Acknowledgment

We thank National Institutes of Health (CA 100757) for partial support of this work.

Author information

Authors and Affiliations

  1. Department of Chemistry, University of Missouri-Columbia, 125 Chemistry Building, Columbia, MO, 65211, USA

    Anuruddha Rajapakse, Charles L. Barnes & Kent S. Gates

  2. Department of Biochemistry, University of Missouri, Columbia, MO, 65211, USA

    Kent S. Gates

Authors
  1. Anuruddha Rajapakse
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Charles L. Barnes
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Kent S. Gates
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Kent S. Gates.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Rajapakse, A., Barnes, C.L. & Gates, K.S. Synthesis and Crystal Structure of the Azoxydichinyl Helicene, Pyrido[3,2-f]quinolino[6,5-c]cinnoline 5-Oxide Monohydrate. J Chem Crystallogr 41, 1712–1716 (2011). https://doi.org/10.1007/s10870-011-0162-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10870-011-0162-z

Keywords

Search

Navigation