SYNTHESIS OF (±)-13β, 17α-DIETHYL-17β-HYDROXY-GONANO 3,2-C PYRAZOLES AND 2,3-C FURAZANES

In Ihe presence of CH₃ONa,(Ⅱ) was reacted with ethyl formate to give 2-hydroxy-methylene-steroid(Ⅳ) which was made to react with hydrazine hydrate to give the pyrazole(Ⅴ). (Ⅳ) was treated with sodium nitrite and acetic acid(or hydrochloric acid) to afford the 2-hydroxylimino-steroid(Ⅵ) which on further oxidation with hydroxylamine gave the dioxime(Ⅶ). Finally dehydration and cyclization of(Ⅶ) produced the desired furazane(Ⅷ).Using similar reaction, 5β isomer(Ⅹ) and(ⅩⅢ) were also obtained from(Ⅲ).