OXIDATION OF AZASTEROID LACTAMS AND ALCOHOLS WITH BENZENESELENINIC ANHYDRIDE

Reaction of 4-azasteriod .delta.-lactams with benzeneseleninic anhydride (2) in diglyme at 120.degree. C smoothly effects dehydrogenation to the corresponding .DELTA.1 derivatives. Oxidation of 3-aza-A-homo-4a-cholesten-4-one (17) or its saturated analog with 2 proceeds readily in refluxing benzene and affords the corresponding imides and .alpha.-phenylseleno imides. Treatment of 2-aza-5.alpha.-cholestan-3-one, prepared by a new efficient route, with 2 results in both dehydrogenation and imide formation and requires forcing conditions. The different relative propensities of the substrates toward reaction via these 2 pathways are attributed to conformational effects in a seleninamide intermediate. Azasteroid alcohols are cleanly converted to the corresponding ketones with 2 under mild conditions.