Beckmann rearrangement of 3-aza-A-homo-4α-androsten-4,17-dione oxime and 3-oxo-13α-amino-13,17-seco-4-androsten-17-oic 13,17-lactam oxime

Article abstract of DOI:10.1002/jhet.5570200449

Rearragements of 3-aza-A-homo-4α-androsten-4,17-dione oxime produced a mixture of the normal lactam product and the product of a 'second order' cleavage, an unsaturated nitrile. The lactam 3,17α-diaza-A,D-bishomoandrost-4α-ene-4,17-dione was also obtained from the rearrangement of the syn-3-oxo-13α-amino-13,17-seco-4-androsten-17-oic-13,17-lactam oxime. The resolution of syn- and anti-isomers of VIII was effected by column chromatography and their structure was determined by spectral data.