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https://doi.org/10.1002/jhet.5570250604
Copy DOIJournal: Journal of Heterocyclic Chemistry | Publication Date: Nov 1, 1988 |
Citations: 6 |
AbstractBeckmann rearrangement of the geometrical isomer of 5α‐androstanolone oximes gives the 3‐aza‐17β‐hydroxy‐A‐homo‐5α‐androstan‐4‐one and the 4‐aza‐17β‐hydroxy‐A‐homo‐5α‐androstan‐3‐one. These lactams were converted to the corresponding ketones by Jones reagent oxidation. Treatment with hydroxylamine produced the corresponding ketoximes. Beckmann rearrangement of the ketoximes generated the diaza compounds and the corresponding “second order” Beckmann cleavage ω‐cyanoolefin. The mixture of the compounds produced, was separated by column chromatography. The structure of the compounds was apparent from spectral data.
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