Synthesis of specific phenazine derivatives of 2-hydroxyestrogens

For stabilisation 2-hydroxyestrone and 2-hydroxyestradiol-17β are converted to their phenazine derivatives by oxidation with sodium metaperiodate to the 2,3-quinones and subsequent condensation with o-phenylenediamine. The structures of this new class of heterocyclic steroids were established by nuclear magnetic resonance, ultraviolet, infrared and mass spectra. The chemical properties and the chromatographic behaviour of these phenazines are described. The specificity of the oxidation was established by using various oxidants and different estrogens; the condensation was optimised by acetic acid catalysis on a microgram scale.