Investigations on Steroids. IV. Syntheses of Androstano[2, 3-c]-furazans and Related Compounds

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Abstract
Steroids with a furazan ring fused to the 2,3-positions were synthesized. 2,3-Dihydroxyiminoandrostanes(m) prepared from androstan-3-ones (I), via 2-hydroxyimino-3-ketones (IV), or 2,3-diketones (n), werecyclizeddirectly toandrostano[2,3-cjurazans (XVII) by means of alkali, succinic anhydride or thionyl chloride. Alternatively, 2,3-dihydroxyimino compounds (HI) were treated with sodium hypochlorite or lead tetra-acetate to afford the corresponding furazan N-oxides (furoxans) (XXI), which were de-oxygenated to the furazans (XVII) by heating with triethyl phosphite. Similarly, androst-4-eno and androsta-4,6-dieno[2,3-c]furazans (XVII, XDC) were prepared. Syntheses of their derivatives were also described.

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