Abstract
Steroids with a furazan ring fused to the 2, 3-positions were synthesized. 2, 3-Dihydroxyiminoandrostanes (III) prepared from androstan-3-ones (I), via 2-hydroxyimino-3-ketones (IV), or 2, 3-diketones (II), were cyclized directly to androstano[2, 3-c]furazans (XVII) by means of alkali, succinic anhydride or thionyl chloride. Alternatively, 2, 3-dihydroxyimino compounds (III) were treated with sodium hypochlorite or lead tetraacetate to afford the corresponding furazan N-oxides (furoxans)(XXI), which were deoxygenated to the furazans (XVII) by heating with triethyl phosphite. Similarly, androst-4-eno and androsta-4, 6-dieno[2, 3-c]furazans (XVII, XIX) were prepared. Syntheses of their derivatives were also described.
