Conclusions
The reaction of Δ16-20-ketopregnenes with mesitylenesulfonylhydroxylamine leads to 17a-aza- and 17-aza-D-homoandrostanes with an amidine fragment in the D ring and proceeds through a sequence of steps involving the initial attack of the reagent at the 20-keto group, a Beckmann rearrangement of the 20-mesityl-sulfonyloxime formed to Δ16-17-acetylaminoandrostene which undergoes a new regioselective cationotropic rearrangement to give steroid amidines.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2376–2383, October, 1983.
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Kamernitskii, A.V., Turuta, A.M., Fadeeva, T.M. et al. Transformed steroids Communication 134. A new regioselective rearrangement of δ16-steroids into D-homoazaandrostanes. Russ Chem Bull 32, 2141–2148 (1983). https://doi.org/10.1007/BF00955790
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DOI: https://doi.org/10.1007/BF00955790