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Formation of bishomoazasteroids by the beckmann rearrangement
Author(s) -
Camoutsis Charalambos,
Catsoulacos Panayotis
Publication year - 1988
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570250604
Subject(s) - beckmann rearrangement , chemistry , hydroxylamine , reagent , cleavage (geology) , stereochemistry , organic chemistry , oxime , geotechnical engineering , fracture (geology) , engineering
Beckmann 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.