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Synthesis of 1,2-Bis(8′-quinolinyl)ethyne and X-ray Characterization of Its Rearranged Oxidation Product 2-Quinoline-8-yl-pyrrolo[3,2,1-ij]quinoline-4-one

Journal of Chemical Crystallography volume 42, pages 1080–1084 (2012)Cite this article

Abstract

The synthesis of 1,2-bis(8′-quinolinyl)ethyne (C20H12N2) using 1,2-bis(tri-n-butylstannyl)ethyne as acetylene precursor is described. The compound was found to be unstable on silica gel for chromatography and the unexpected rearranged oxidation product 2-quinoline-8-yl-pyrrolo[3,2,1-ij]quinoline-4-one (C20H12N2O) was isolated and characterized. The X-ray structure of 2-quinoline-8-yl-pyrrolo[3,2,1-ij]quinoline-4-one is orthorhombic with a = 8.0909(14), b = 12.570(2), c = 13.807(3)Å, α = γ = β = 90o and space group P 21 21 21. The two polycyclic ring systems are coplanar with a torsional angle of approximately 65o between the two rings.

Graphical Abstract

The synthesis of 1,2-bis(8-quinolinyl)ethyne and the isolation and X-ray characterization of the rearranged oxidation product 2-quinoline-8-yl-pyrrolo[3,2,1-ij]quinoline-4-one (C20H12N2O) is reported.

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Scheme 1
Scheme 2
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Acknowledgments

The Missouri State University Provost Incentive Fund funded the purchase of the X-ray diffractometer. The Northern Plains Undergraduate Research Center and the Arlen Viste Fellowship (Augustana College) assisted in funding this project.

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Authors and Affiliations

  1. Chemistry Department, Missouri State University, 901 South National Avenue, Springfield, MO, 65897, USA

    Eric Bosch

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

    Charles L. Barnes

  3. Chemistry Department, Augustana College, 2001 South Summit Avenue, Sioux Falls, South Dakota, SD, 57197, USA

    Michael Stutelberg & Barrett Eichler

Authors
  1. Eric Bosch
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  2. Charles L. Barnes
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  3. Michael Stutelberg
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  4. Barrett Eichler
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Correspondence to Eric Bosch or Barrett Eichler.

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Bosch, E., Barnes, C.L., Stutelberg, M. et al. Synthesis of 1,2-Bis(8′-quinolinyl)ethyne and X-ray Characterization of Its Rearranged Oxidation Product 2-Quinoline-8-yl-pyrrolo[3,2,1-ij]quinoline-4-one. J Chem Crystallogr 42, 1080–1084 (2012). https://doi.org/10.1007/s10870-012-0351-4

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  • DOI: https://doi.org/10.1007/s10870-012-0351-4

Keywords

  • 1,2-Bis(8′-quinolinyl)ethyne
  • Quinoline-4-one
  • Oxidative rearrangement