Abstract
Treatment of 2,4,8,10-tetranitro-6(5H)-phenanthridinone with hexamethylphosphoric triamide leads to intermolecular nucleophilic substitution of the nitro group by a hydroxy group, the source of which is the water contained in the solvent, to give 10-hydroxy-2,4,8-trinitro-6(5H)-phenanthridinone. An intramolecular interaction with the participation of a proton of the aromatic ring and an oxygen atom of the hydroxy or acetoxy group of the 10-hydroxy- or 10-acetoxy-2,4,8,-trinitro-6(5H)-phenanthridinone, the properties of which are characteristic for an intramolecular hydrogen bond, was detected by x-ray diffraction analysis and PMR spectroscopy.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 314–319, March, 1987.
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Andrievskii, A.M., Poplavskii, A.N., Dyumaev, K.M. et al. Synthesis and structures of 10-hydroxy- and 10-acetoxy-6(5H)phenanthridinones. Chem Heterocycl Compd 23, 261–266 (1987). https://doi.org/10.1007/BF00761980
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DOI: https://doi.org/10.1007/BF00761980