Abstract
Steroidal oxazoles, imidazoles, and triazoles were synthesized for biological studies. 2α-Acetoxy-or 2α-bromo-3-ketones of androstane and cholestane series were converted into 2'-methylsteroidal [3, 2-d] oxazoles (III) by reaction with ammonium acetate. Reductive acetylation of 2-hydroxyimino-3-oxo steroids (V) gave 2α-acetamido-3-ketones (VI) which were cyclized by the use of sulfuric acid to 2'-methyl-steroidal [2, 3-d] oxazoles (XI). 2'-methyl-steroidal [2, 3-d] imidazoles (XII) were prepared from VI by reaction with ammonium acetate. 2α-Amino-3-ketone hydrochlorides, obtained by catalytic hydrogenation of V, were converted by reaction with thiocyanate into steroidal [2, 3-d] imidazoline-2'-thiones which were desulfurized to afford imidazoles (XIV). Androst-4-eno[2, 3-d]-triazoles (XX) were prepared from the 2-acetoxymethylene-3-ketone via the 2-hydroxyimino-3-one hydrazone by application of the established procedures. The ORD (and CD) data of VI and the corresponding 3β-alcohol (VIIId) are presented.
