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
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 65° 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. Open image in new window
Chemistry and Biochemistry
1, 2-Bis(8′-quinolinyl)ethyne, quinoline-4-one, oxidative rearrangement
Bosch, Eric, Charles L. Barnes, Michael Stutelberg, and Barrett Eichler. "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 42, no. 10 (2012): 1080-1084.
Journal of Chemical Crystallography