Abstract
The structures of the tautoraers of 2-hydroxyazabenzanthrones were investigated as compared with those of benzanthrone and the tautomers of 2-quinolone and 3-iso-quinolone by a quantum-chemical method. In the lactam form of 2-hydroxy-3-aza-benzanthrone the bonds in both extreme rings are equalized, and the heteroring is less aromatic than in 2-pyridone and 2-quinolone. In the lactam form of 2-hydroxy-1-azabenzanthrone and equality of the bonds in the extreme ring, as in benzanthrone, is disrupted, and the heterocyclic fragment is similar with respect to the distribution of the bonds and charges to the isolated 3-isoquinolone molecule. The data obtained are in good agreement with the chemical and spectral properties of 2-hydroxyazabenzanthrones.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 803–809, June, 1981.
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Mikhailova, T.A., Zaitsev, B.E., Sheban, G.V. et al. Electronic structure of 2-hydroxyazabenzanthrones. Chem Heterocycl Compd 17, 594–599 (1981). https://doi.org/10.1007/BF00503486
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DOI: https://doi.org/10.1007/BF00503486